Chemistry and Materials Research ISSN 2224- 3224 (Print) ISSN 222 - !" # ($nline) %ol.3 No.&!' 2!

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Electrochemical Synthesis, Characterization and Electrochemical behaviour of New Conducting Copolymers of 2methoxyaniline-co-2, -dihydrothieno! ,"-b#!$,"#dioxine-2carboxylic acid
M(tla) Shediad *l-+ahdali& *,del *-i- .asem Mohammad /,arah20 Mohamed hamdy Mohamed 1elal2 &. Chemistry 2e3artment' 4ac(lty o5 Science' 6ing *,d(la-i- 7ni8ersity' P$ ,o9 :!2!!' /eddah 2& :"' 6ingdome o5 Sa(di 2. Chemistry 2e3artment' 4ac(lty o5 *rts and Science' Northern ;orders 7ni8ersity' P$ ,o9 &32&' *r*r "&43&' Ra5ha cam3(s' 6ingdome o5 Sa(di *ra,ia 0 <-mail o5 the corres3onding a(thor= +,r.a,ed>yahoo.com %bstract <lectroacti8e cond(cting co3olymers o5 2-metho9yaniline and 2'3-dihydrothieno?3'4-,@?&'4@dio9ine-2car,o9ylic acid (<2$A car,o9ylic acid) molec(les were 3re3ared in non-a)(eo(s sol(tion ,y electrode 3otential cycling. Co3olymeri-ation was carried o(t at di55erent 5eed concentrations o5 the monomers on a gold electrode. 4o(r di55erent 5eed concentrations were (sed to 3re3are 5o(r di55erent co3olymers. Ahe o,tained co3olymers were characteri-ed with cyclic 8oltammetry and in5rared s3ectrosco3y. Ahe 3re3ared hom3olymers and co3olymers were in8estigated with in sit( cond(cti8ity meas(rements. Awo transitions were o,ser8ed in the in sit( cond(cti8ities o5 the co3olymers. &eywords' in sit( cond(cti8ity' 2-metho9yaniline' <2$A car,o9ylic' co3olymers $( )ntroduction Recently' electrically cond(cting 3olymers ha8e many 3otential a33lications' s(ch as new materials 5or ,attery electrodes ($tero B Cantero &"""' *manoC(ra et al. 2!!&' D(r(nathan et al. &""")' s(3erca3acitors (Mastragostino et al. 2!!2)' chemical sensors (D(3ta et al. 2!!#' Sot-ing et al. 2!!!' Ein et al. &"""' Nicolas2e,arnot et al. 2!!3). ion sie8ing (Shinohara et al. &":#)' corrosion 3rotection ($hts(Ca 2!&2' Darca et al. 2!!2)' and microwa8e shielding (Patil et al. 2!&2' ;(cCley B <asho8 &""#). *mong cond(cting 3olymers' 3oly(2metho9yaniline) (PM*) has attracted m(ch attention. ;ereCet et al. (2!! ) ha8e ,een st(died its anti-corrosi8e 3ro3erties. Cha(dhari and Patil (2!!:) ha8e ,een in8estigated the corrosion 3rotecti8e o5 ,i-layered com3osites o5 3olyaniline and PM* on low car,on steel. PM* ha8e ,een synthesi-ed 5or de8elo3ed 5or de8elo3ment o5 gl(cose ,iosensor (Sa8ale B Shirsat 2!!"). Ahe corrosion-3rotecti8e 3er5ormance o5 nano P$*FalCyd coatings has ,een in8estigated on mild steel (/adha8 et al. 2!&!). Co3olymeri-ation o5 two di55erent monomers that ,ear di55erent 5(nctional gro(3s leads to modi5ied co3olymers that 3ossessing interesting 3ro3erties. se8eral st(dies incl(ded co3olymeri-ation o5 aniline-thio3hene' 5(ranthio3hene and aniline-3yrrole monomers ha8e ,een re3orted recently (*r+omandi B 1ol-e 2!!:' *laChras B 1ol-e 2!!:' %ogel B 1ol-e 2!! ' *ntony B /ayaCannan 2!&&). Ahe 3rimary ad8antage o5 co3olymeri-ation is that it leads to a material in which its 3ro3erties can ,e reg(lated ,y ad+(sting the ratio o5 the concentration o5 monomers in the 5eed. Ah(s co3olymeri-ation is an im3ortant method to modi5y the 3ro3erties o5 indi8id(al homo3olymers. In the 3resent st(dy' 2-metho9yaniline (M*) and <2$A car,o9ylic acid (<2$AC*) ha8e ,een se-lected as monomers 5or 3er5orming electrochemical co3olymeri-ation (4ig(re &) in !.&M Aetra,(tylammoni(m tetra5l(oro,orate (A;*A4;)Facetonitrile medi(m. Cyclic 8oltammetry was (sed to de3osit 3olymeric 5ilms on gold worCing electrode and s(,-se)(ent characteri-ation. Co3olymers were also characteri-ed ,y In5rared s3ectrosco3y. Ahe co3olymers and homo3olymers were in8estigated ,y in sit( cond(cti8ity meas(rements.

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Chemistry and Materials Research ISSN 2224- 3224 (Print) ISSN 222 - !" # ($nline) %ol.3 No.&!' 2!&3

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4ig(re &. <lectrochemical coolymeri-ation o5 M* and <2$AC* molec(les. 2( Experimental *ll chemicals were o5 analytical grade. Ahe 2-metho9yaniline (4l(Ca) and <2$A-car,o9ylic acid (*ldrich) (sed as recei8ed. Aetra,(tylammoni(m tetra5l(oro,orate (A;*A4;G *ldrich' Stein-heim' DermanyG ""H) was dried in 8ac(o at :!IC 5or 24 h. *cetonitrile (MercC' 2armstadt' DermanyG anhydro(s' J&! 33m 12$) was (sed witho(t 5(rther 3(ri5ication. Ahe electro3olymeri-ation was 3er5ormed (nder 3otentiodynamic conditions at a scan rate o5 &!! m%Fs and ,y (sing !.&M A;*A4; in acetonitrile as s(33orted electrolyte and in a one-com3artment' three-electrode cell at room tem3erat(re. Ahe worCing electrode (sed is gold disc electrode' the co(nter electrode is 3latin(m wire and the re5erence electrode is *gF*gCl (which has a 3otential o5 K!.22 8s S1<). Ahe worCing gold disC electrode (!.2 cm2) was 3olished down to !.3 L with *l2$3' rinsed withG acetone' distilled water and 5inally with ethanol. Cyclic 8oltammetry was 3er5ormed with a com3(teri-ed SP ! 3otentiostat (5rom ;io Eogic Science Instr(ments' 4rance). *ll sol(tions were 5reshly 3re3ared' 3(rged with nitrogen (""."""H)' and all e93eriments were 3er5ormed at room tem3erat(re (2! MC). Ahe 4o(rier trans5orm in5rared (4AIR) s3ectra o5 the homo3olymer and co3olymer 5ilms were recorded with 6;r 3ellets with a PerCin<lmer 4AIR &!!! s3ectrometer at a 2 cm-& resol(tion. 4or these meas(rements' the 5ilm was scra3ed o55 5rom the electrode and dried. In the In sit( cond(cti8ity meas(rements the 3olymer was de3osited on a two-stri3s gold electrode in a three electrode cell with a s3ecially designed electronic circ(it s(33lying &! m% 2C 8oltage across the two gold stri3s (1ol-e and B Ei33e &""!). In this meas(rements the two gold stri3s o5 the electrode are se3arated ,y a ga3 o5 a 5ew micrometers that is easily ,ridged thro(gh de3osition o5 cond(cting 3olymers' when ,oth electrodes are connected electrically together and (sed as the worCing electrode. *ltho(gh this set(3 is associated with the 3ro,lem o5 ens(ring the identical thicCnesses o5 5ilms across the ins(lating ga3' ne8ertheless' a33ro9imately re3rod(ci,le res(lts can ,e o,tained ,y ad+(sting the e93erimental conditions as 8ery thin 5ilms can (s(ally 5orm good ,ridges o8er the ga3 ,etween the electrodes. ( *esults and +iscussion 3.1 Electrochemical oxidation of OA and EDOTCA 4ig(re 2 shows the electroo9idation o5 M* (&! mM) in !.& M A;*A4; sol(tion when cycling the 3otential ,etween -!.2 and &. ! % at a scan rate o5 &!! m%Fs. In the 3ositi8e swee3 one anodic 3eaCs are well de5ined at !."34 % is ca(sed ,y the o9idation o5 NN12 o5 M*. Ahe anodic 3eaC d(e to electro o9idation o5 &! mM M* started aro(nd K!.#O3 % (8ers(s *gF*gCl)' in !.& M A;*A4;Facetonitrile sol(tion. Ahe o9idation 3eaC o5 M* at 3latin(m worCing electrode were re3orted ,y $-yilma- et al. (2!!:) at K!."3 % 5or low scan rate and at a33ro9. K&.2&% 5or high scan rate which is in 3er5ect agreement with o(r res(lt. $n the negati8e swee3 the cyclic 8oltammogram is not showing any corres3onding red(ction 3eaCs.

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Chemistry and Materials Research ISSN 2224- 3224 (Print) ISSN 222 - !" # ($nline) %ol.3 No.&!' 2!&3

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4ig(re 2. Cyclic 8oltammogram 5or electrolysis o5 sol(tion containing &! mM M* in !.& M A;*A4; in acetonitrile ,y cycling the 3otential ,etween -!.2 and &. % at a scan rate o5 &!! m%Fs. 4ig(re 3 shows the electro-o9idation o5 <2$AC* (&! mM) in !.& M A;*A4;F acetonitrile sol(tion when cycling the 3otential ,etween -!.3 and &.# % at a scan rate o5 &!! m%Fs. In the 3ositi8e swee3 one anodic 3eaCs are well de5ined at &. 4" % is ca(sed ,y the o9idation o5 the s(l5(r atom o5 <2$AC*. Ahe 3osition o5 this anodic 3eaC is higher with &" m% than that re3orted ,y $cam3o et al. (2!!#) 5or the o9idation o5 &! mM 3'4-ethylenedio9ythio3hene (<2$A) in a sol(tion o5 !.& M EiCl$4 in acetonitrile and at steel electrode. $cam3o et al. (2!!#) also re3orted that a second anodic 3eaC corres3onds to the o9idation o5 <2$A located at higher 3otential 8al(e and o8erla3s with the o9idation o5 the medi(m. ;oth' the anodic 3eaC that o,ser8ed in this st(dy 5or <2$AC* and the one that o,tained ,y $cam3o et al.(2!!#) 5or <2$A are higher than that re3orted elsewhere (SaraP et al. 2!!3' %asantha B Phani 2!!2). *ll o5 the di55erences ,etween the 3osition o5 the anodic 3otential that o,ser8ed in o(r st(dy 5or <2$AC* and that re3orted 5or <2$A in 3re8io(s worCs can ,e attri,(ted to two reasons. Ahe 5irst one is the str(ct(ral di55erence ,etween <2$A and <2$AC*. Ahe second one is that we (sed in o(r e93eriments a di55erent s(33orting electrolyte and worCing electrode than that (sed in the re3orted worCs 5or electrochemical ,eha8ior o5 <2$A.
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4ig(re 3. Cyclic 8oltammogram 5or electrolysis o5 sol(tion containing &! mM <2$AC* in !.& M A;*A4; in acetonitrile ,y cycling the 3otential ,etween -!.3 and &.# % at a scan rate o5 &!! m%Fs. 3.2 Electrochemical homopolymerization of MA Ahe m(ltiswee3 cyclic 8oltammograms (4! cycles) o5 & mM M* in !.& M A;*A4;Facetonitrile sol(tion at gold electrode are dis3layed in 4ig(re 4. It was o,ser8ed 5rom 4ig(re 4 that the o9idation 3eaC o5 the M* in the 5irst cycle disa33ears and anew anodic and cathodic c(rrents increase in the 3otential region ,etween -2!!.! and &.!O

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% with each s(,se)(ent cycle. $,8io(sly' Ahese c(rrents are corres3onding growth o5 the PM* 5ilms at the gold s(r5ace. In the 3ositi8e swee3 in the cycles o5 4ig(re 4 an anodic ,eaCs o,ser8ed at !.3:4 and !.:O %. In the negati8e swee3 the cyclic 8oltammograms are showing a two corres3onding red(ction 3eaCs at -!.!!: and !. O& %. Ahese 3eaCs are ca(sed ,y o9idations and red(ctions o5 the 3olymers 5ilms that growth at the gold s(r5ace.
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4ig(re 4. Cyclic 8oltammograms 5or electrolysis o5 sol(tion containing &! mM M* in !.& M A;*A4; in acetonitrile ,y cycling the 3otential ,etween -!.2 and &. % at a scan rate o5 &!! m%Fs. Ahe PM* modi5ied electrode was then immersed into monomer 5ree electrolyte sol(tion and its cyclic 8oltammogram was recorded in the 3otential range ,etween -!.2 and &.2! % as de3icted in 4ig(re . Ahe 5ilm was 8ery sta,leG it did not lose its electrochemical acti8ity a5ter re3etiti8e cycling ,oth at 8ery low and 8ery high scan rates in this 3otential region. Ahe cyclic 8oltammogram o5 the PM* 5ilm (4ig(re ) shows a two anodic 3eaCs at !.3O& and &.!#O % and its corres3onding cathodic wa8es at !.2&O and !.O!O %. Ahis electrochemical ,eha8ior are totally di55erent 5rom the electrochemical ,eha8ior o5 the M* monomers which are descri,ed in the 4ig(re 2. Ahis di55erence is an e8idence o5 the 5ormation o5 the 3olymer 5ilm at the gold s(r5ace. ;ereCet et al. (2!! ) re3orted that the PM* 5ilm e9hi,its one ,road o9idation and one red(ction 3eaCs in the ,lanC sol(tion. In them res(lts the ,road anodic 3eaC was o,ser8ed in the 3otential range ,etween !.3 to &.# % which in the 3otential range o5 the two anodic 3eaCs that o,ser8ed in o(r st(dy. Ahe di55erence ,etween o(r res(lt and that o5 ;ereCet et al (2!!3) might ,e related to the di55erence in the electrolyte sol(tions that they (sed in them e93eriments 5rom that one we (sed in this st(dy. In o(r st(dy we (sed !.& M A;*A4; in acetonitrile as s(33orting electrolyte. Ahe s(33orting electrolyte (sed in the e93eriments o5 ;ereCet et al. is 2!mM 1Cl$4 in !.&M tetra,(tylammoni(m 3erchlorate. Ahe (se o5 this s(33orting electrolyte might ca(se an o8erla3 ,etween tow anodic 3eaCs to a33ear as ,road one as re3orted in the ;ereCet et al. (2!! ) res(lt. * two well-resol8ed anodic 3eaCs in the cyclic 8oltammograms recorded d(ring the synthesis o5 PM* 5ilm in a)(eo(s sol(tion o5 12S$4 as s(33orting electrolyte are re3orted elsewhere (;orole et al. 2!! ). Patil et al. (&""O) were re3orted the di55erence ,etween the electrochemical ,eha8ior o5 PM* in the 3resence and a,sence o5 NaCl. Ahey o,tained a well distinct 3eaCs in the cyclic 8oltammogram o5 the PM* that de3osited in the 3resence o5 NaCl in the de3osition medi(m. Qhile in the a,sence o5 NaCl in the the de3osition medi(m they o,ser8ed that the 3eaCs o5 the cyclic 8oltammogram are not well-resol8ed.

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4ig(re . Cyclic 8oltammograms 5or electrolysis o5 PM* in !.& M A;*A4;F acetonitrile sol(tion (in monomer 5ree electrolyte sol(tion) at a scan rate o5 &!! m%Fs 3.3 Electrochemical homopolymerization of EDOTCA 4ig(re # shows the m(ltiswee3 cyclic 8oltammograms (4! cycles) o5 &! mM <2$AC* in !.& M A;*A4;Facetonitrile sol(tion at gold electrode. Ahe 5ormation and growth o5 the 3oly(<2$AC*) 3olymer (P<2$AC*) 5ilm can easily ,e seen in this 5ig(re. Ahe o9idation and red(ction 3eaCs o5 the 5ilm increase in intensity as the 5ilm grows. In the m(ltiswee3 cyclic 8oltammograms o5 4ig(re # the anodic c(rrent that corres3onds o5 the 3olymer 5ilm growth a33ears in the range ,etween -!.! 2 and !.:3 % and its corres3onding cathodic one a33ears in the range ,etween -!.2: and !.#:# %. Ahis wide range 3otential o5 electro3olymeri-ation is also o,ser8ed in the in the cyclic 8oltammograms that recorded 5or electro3olymeri-ation o5 <2$A in di55erent s(33orting electrolytes and at di55erent worCing electrodes as re3orted ,y se8eral 3re8io(s worCs ($cam3o et al. 2!!#' SaraP et al. 2!!3' *hmed et al. 2!&2).
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4ig(re #. Cyclic 8oltammograms 5or electrolysis o5 sol(tion containing &! mM <2$AC* in !.& M A;*A4; in acetonitrile ,y cycling the 3otential ,etween -!.3 and &. % at a scan rate o5 &!! m%Fs. * cyclic 8oltammogram was recorded 5or the gold electrode that co8ered with a layers o5 the 3olymer P<2$AC* layers in a monomer 5ree electrolyte sol(tion in the 3otential range ,etween -!.3 and &.& % as shown in 4ig(re O. Ahe 5ilm was 8ery sta,leG it did not lose its electrochemical acti8ity a5ter re3etiti8e cycling ,oth at 8ery low and 8ery high scan rates in this 3otential region. Ahe cyclic 8oltammogram o5 the P<2$AC* 5ilm (4ig(re O) shows two anodic 3eaCs at !.!#2 % and at !. 4& % and its corres3onding cathodic 3eaC at !.!2# % and at !.423 %. Ahis electrochemical ,eha8ior are totally di55erent 5rom the electrochemical ,eha8ior o5 the <2$AC* monomers which are descri,ed in the 4ig(re 3. Ahis di55erence is an e8idence o5 the 5ormation o5 the 3olymer 5ilm at the gold s(r5ace. Ahe two redo9 3rocesses o5 4ig(re O located at higher electrode 3otentials than that re3orted ,y SaraP et al. (2!!3) 5or 3oly(<2$A). Ahey 3olymeri-ed <2$A 5rom a 23

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sol(tion o5 !.!& M o5 monomer concentration and in a s(33orting electrolyte that consist o5 !.& M EiCl$4F3ro3ylene car,onate at the car,on 5i,re microelectrode. Ahese condition o5 3olymeri-ation are di55erent 5rom that (sed in o(r st(dy 5or elctro3olymeri-ation o5 <2$AC*. Ahere5ore the two redo9 3rocesses that o,ser8ed in o(r st(dy are located at higher electrode 3otential than that re3orted ,y SaraP et al. *lso the 3resence o5 car,o9ylic acid gro(3 as s(,stit(ent in P<2$AC* might ,e a second reason 5or the shi5ts o5 the two redo9 3rocesses to a higher electrode 3otentials as com3ared to that o5 3oly(<2$A). It sho(ld ,e mentioned that the sha3e o5 cyclic 8oltammogram o5 the P<2$AC* that o,tained in o(r st(dy is 8ery similar to that re3orted 5or 3oly(<2$A) (SaraP et al. 2!!3).

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4ig(re O. Cyclic 8oltammograms 5or electrolysis o5 P<2$AC* in !.& M A;*A4;, acetonitrile sol(tion (in monomer 5ree electrolyte sol(tion) at a scan rate o5 &!! m%Fs 3.4 Electrochemical copolymerization of EDOTCA and MA Qe (sed se8eral di55erent 3olymeri-ation sol(tions with di55erent 5eed ratios to 3re3are 5o(r new co3olymers consists o5 M* and <2$AC* ,y (sing cyclic 8oltammetry method. Ahe co3olymers' synthesi-ed with 8ario(s 5eed ratios' were la,eled co3olymer * (C$P*' 2!mM M* K mM <2$AC*)' co3olymer ; (C$P;' 2!mM M* K &!mM <2$AC*)' co3olymer C (C$PC' 2!mM M* K & mM <2$AC*) and co3olymer 2 (C$P2' mM M* K 2!mM <2$AC*). 4ig(re : a-d show the cyclic 8oltammograms recorded d(ring the synthesis o5 the a,o8e mentioned co3olymers. Ahe o8erall o,ser8ations and res(lts ,ased on cyclic 8oltammograms o5 4ig(re : are concl(ded as 5ollows. In each case it was o,ser8ed an anodic and cathodic c(rrents increase with each s(,se)(ent cycle. Ahese c(rrents corres3onding growth o5 the co3olymers at the gold s(r5aces. Ahe cyclic 8oltammograms o5 4ig(re : are di55erent 5rom that o5 indi8id(al homo3olymers (4ig(re 4 and #). Ahis di55erence is nota,le when the concentration o5 <2$AC* monomer in the 3olymeri-ation sol(tion ,ecomes 8ery close to that o5 M* monomer as in the case o5 C$P; (4ig(re :,) and C$PC (4ig(re :c). Qhen the concen-tration o5 <2$AC* monomer in the 3olymeri-ation sol(tion is 8ery low as com3ared to that o5 M* monomer the cyclic 8oltammograms (4ig(re :a) ,ecomes 8ery similar to that o5 homo3olymer M* (4ig(re 4). Ahis indicates that high M* (nits are incor3orated into this co3olymer chains. Qhen the concentration o5 <2$AC* monomer in the 3olymeri-ation sol(tion is 8ery high as com3ared to that o5 M* monomer the cyclic 8oltammogram (4ig(re :d) ,ecomes 8ery similar to that o5 homo3olymeri-ation o5 <2$AC* (4ig(re #). Ah(s C$P2 are e93ected to ha8e more <2$AC* (nits at the co3olymer ,acC,one than that o5 M* (nits. Denerally in all cases these di55erence is 5(rther s(33orts the 5ormation o5 co3olymers and th(s' we got 5o(r di55erent co3olymers ,y changing the monomers 5eed ratios in the 3olymeri-ation sol(tion.

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4ig(re :. Cyclic 8oltammograms 5or electrolysis o5 sol(tion containing (a) 2! mM M* K mM <2$AC* in !.& M A;*A4;Facetonitrile (, ) 2! mM M* K &! mM <2$AC* in !.& M A;*A4;Facetonitrile (c ) 2! mM M* K & mM <2$AC* in !.& M A;*A4;Facetonitrile (d ) mM M* K 2! mM <2$AC* in !.& M A;*A4;Facetonitrile at a scan rate o5 &!! m%Fs. Ao determine the electrochemical ,eha8ior o5 the co3olymers C$P*' C$P;' C$PC and C$P2 a cyclic 8oltammograms were recorded 5or the gold electrodes that co8ered with the layers o5 each co3olymer in a monomer 5ree electrolyte sol(tion. Ahe cyclic 8oltammograms are shown in 4ig(re "a-d. 4ig(re " shows that the electrochemical ,eha8iors o5 co3olymers C$P*' C$P;' C$PC and C$P2 are not identical. 4ig(re "a shows a ty3ical cyclic 8oltammogram o5 a co3olymer o,tained 5rom a !.& M A;*A4;Facetonitrile sol(tion containing 2! mM M* and mM <2$AC*. Awo o8erla3s anodicFcathodic 3eaCs co(3le a33ear with the co3olymer 5ilm at a 3osition )(ite di55erent 5rom the 3ositions o,ser8ed with PM* (4ig(re ) and P<2$AC* (4ig(re O). Ahe anodic 3eaCs a33ear at !.#3O and !." " % and its corres3onding cathodic 3eaCs a33ear at !.2O# and !. 3 %. Ahe cathodic and anodic c(rrents o5 this co3olymer are 8ery similar to that 5o(nd with the homo3olymer PM* and higher than that 5o(nd with the P<2$AC*. Ahis im3lies that the electrochemical acti8ity (redo9 ca3acity) o5 this co3olymer is 8ery close to that o5 the PM*. Ahe di55erence ,etween the two anodicFcathodic 3eaC co(3les 3ositions ,etween C$P* and PM* sho(ld ,e attri,(ted to the e55ects o5 the 3resence o5 small amo(nt o5 the <2$AC* monomer in the 3olymeri-ation sol(tion that (sed in the case C$P*. *s the concentration o5 the <2$AC* monomers increased in the 5eed ratio o5 the 3olymeri-ation sol(tion that (sed 5or the co3olymers' the di55erence in electrochemical ,eha8ior o5 the co3olymers 5rom that o5 homo3olymers ,ecomes nota,le. Ahis sit(ation is o,ser8ed in the case o5 C$P; and C$PC. * higher c(rrent densities corres3onding to the anodic and cathodic 3eaCs are o,ser8ed 5or the co3olymers C$P; (4ig(re ",) and C$PC (4ig(re "c) than that o5 homo3olymers (4ig(re and O ) and other co3olymers (4ig(re "a and "d). Ahis im3lies that the electrochemical acti8ity (redo9 ca3acity) is higher 5or these co3olymers. * second o,ser8ation is that the cyclic 8oltammograms o5 these co3olymers shows three 3oorly resol8ed anodicFcathodic 3eaC co(3les. Ahe anodic 3eaCs corres3onding to the o9idation o5 C$P; a33ear at !. 3"' !."24 and &.3O4 % and its corres3onding cathodic 3eaCs a33ear at !.!4 ' !.O:4 and &.2O %. 4or the C$PC the anodic 3eaCs a33ears at !.4:4' &.&3& and &.3 " % and its corres3onding cathodic 3eaCs a33ears at -!.!"#' !.3&O and &.&42 %. Qhen we (sed higher concentration o5 the <2$AC* monomers in the 5eed ratio o5 the 3olymeri-ation sol(tion than that o5 M* monomers as in the case o5 C$P2 (4ig(re "d)' the cyclic 8oltammogram shows only one anod-icFcathodic 3eaC co(3le. Ahe anodic 3eaC a33ears at !.#!4 % and 2

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its corres3onding cathodic one a33ears at !.2!: %. Ahe cathodic and anodic c(rrents o5 this co3olymer are 8ery similar to that 5o(nd with the homo3olymer P<2$AC* and lower than that 5o(nd with the other co3olymers.
0.0004

( )

A P O C

( )

B P O C b

0.0001
0.0002

A /

A /

I
0.0000

0.0000

-0.0002

-0.0001 -1.0

-0.5

0.0

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1.5

2.0

-1.0

-0.5

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l C g A / g A

0.00015

( )
0.0004

( )

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C P O C
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A /

0.0000

A /

I
0.00000 -0.00005

-0.0004

-1.0

-0.5

0.0

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1.0

1.5

2.0

-0.00010 -1.0

-0.5

0.0

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4ig(re ". Cyclic 8oltammograms 5or the gold electrodes co8ered with (a) C$P*' (,) C$P;' (c) C$PC and (d) C$P2 in !.& M A;*A4;Facetonitrile sol(tion (in monomer 5ree electrolyte sol(tion) at a scan rate o5 &!! m%Fs 3.5 T!" mea#$rement# Ahe co3olymer was characteri-ed ,y 4AIR. Ahe 4AIR s3ectra o5 PM*' P<2$AC*' C$P*' C$P;' C$PC and C$P2 are shown in 4ig(re &!a-5. *ssignments o5 the o,ser8ed ,ands are listed in Aa,le & and ,ased on literat(re data ( %arsRnyi &"O4' 2ollish et al. &"O4' Ein-%ien et al. &""&' EarCin 2!&&' St(art 2!!4). Ahe s3ectr(m o5 P$* (4ig(re "a' Aa,le &) shows a 3eaCs at O3#' &!32' &!4 ' && !' &3O: and &4#! cm-& which are assigned 5or S(C1) o5 aromatic ring' T(ring)' U(Ph-$-C)' U(C-N-C)' T(C1) o5 aromatic ring and U(ring)' res3ecti8ely. In the s3ectr(m o5 P<2$AC* (4ig(re &!,' Aa,le &)' there are se8eral 3eaCs a33ears at :2!' :# ' &2 3' & !3 and &#&" cm-& that assigned 5or Vas(C12)' thio3hene ring ,reathing' U(C-$-C) o5 ethylenedio9y moiety' U(ring) and U(ring)' res3ecti8ely. Ahese PeaCs are clearly disting(isha,le 5rom that o5 P$*. Most o5 the a,o8e mentioned characteristic 3eaCs o5 PM* and P<2$AC* are also a33eared in the s3ectra o5 the co3olymers C$P* (4ig(re &!c)' C$P; (4ig(re &!d)' C$PC (4ig(re &!e) and C$P2 (4ig(re &!5). Ahis 5eat(re indicated that these co3olymers contains ,oth $* and <2$AC* (nits. Its was nota,le that most o5 the 3aeCs o5 C$P2 (4ig(re "5) were common 5or P<2$AC*. Ahis res(lt con5irms that the the <2$AC* (nits are dominant in the co3olymer C$P2. Ahis concl(ssion con5irms o(r res(lt that disc(ssed a,o8e in the case o5 electrochemical ,eha8io(r o5 this co3olymer. It sho(ld ,e mensitioned that there are two new 3eaCs a33eared only in the co3olymers s3ectra. Ahe 5irst one a33eared at #"3' #::' #"4' and #O: cm-& in the s3ectr(m o5 C$P*' C$P;' C$PC and C$P2' res3ecti8ely. Ahe second 3eaC a33eared at & : ' & :O and & :4 cm-& in the s3ectr(m o5 C$P*' C$P; and C$PC' res3ecti8ely. Since these 3eaCs are missed in the s3ectra o5 the homo3olymers it was 3ro,a,ly that these 3eaCs are concerning the intramolec(lar interaction ,etween M* and <2$A*C (nits at the co3olymers ,acC,one.

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0.20

0.25

( )

A M P

( )

A C T O D E P

0.15

0.20

Absorption / -

0.10

Absorption / 500 750 1000 1250

-1

0.15

0.05

0.10

1500

1750

2000

500

750

1000

1250
-1

1500

1750

2000

Wavenumbers / cm

Wavenumbers / cm

0.30

( )

A P O C
0.15

( )

B P O C

0.25

Absorption / -

Absorption / 500 750 1000 1250

-1

0.20

0.10

0.15

0.10 0.05 0.05

1500

1750

2000

500

750

1000

1250
-1

1500

1750

2000

Wavenumbers / cm

Wavenumbers / cm

( )
0.15

0.30

C P O C

()
0.25

D P O C f

0.20 Absorption / 0.10 Absorption / 500 750 1000 1250

-1

0.15

0.10 0.05 0.05

1500

1750

2000

500

750

1000

1250
-1

1500

1750

2000

Wavenumbers / cm

Wavenumbers / cm

4ig(re &!. In5rared s3ectr(m o5 the co3olymers' resol(tion 4 cm-&' 32 scans.

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Aa,le&. *ssignment o5 8i,rational modes o5 the homo3olymers and co3olymers.

Mode S(ring)a V(C-($1)), S(ring)a n.a. n.a. n.a. Sas(C12), n.a. n.a. S(C1)a n.a. Vas(C12), ring ,reathing, S(C1)a T(ring)a U(Ph-$-C)a U(C-S), T(C1)a U(C-N-C)a n.a. U(C-$-C), T(ring)a U(ring), T(C1)a U(ring), U(ring)a U(ring)a U(ring), U(ring), n.a. U(ring), U(CW$), n.a. n.a. n.a.
a

PM* 4&2 4"" #& O3# O"& ::O &!32 &!4 &!:# && ! &2:3 &3O: &4#! &4:3 -

P<2$AC* 44 2& #&3 # " O&# :2! :# &! # &&O2 &2 3 &32O &43! & !3 & 3# &#&" &#O4 &O:3 &"23 &" 3

In5rared ;and Position (cm-&) C$P* C$P; 4&3 4O: &O &2 #"3 #:: O42 O3" :3O :22 :## :#O &!2" &!4O &!43 &!"2 && && O &242 &24 &2"2 &32# &3O" &3O: &4#: &4 & & !4 & !: & : & :O &#23 &#23 -

C$PC #"4 O3: :23 :#3 &!2# &!44 && 2 &242 &2"& &3:2 &4 3 & ! & :4 &#24 -

C$P2 442 O: #!# # & #O: O&4 O3# :2& :#2 &!24 &&!! &&O3 &2 4 &32# &42 & !4 &#"& &OO# &"2" &" #

= ,and corres3onding to M* moiety o5 the 3olymerG ,= ,and corres3onding to <2$A moiety o5 the 3olymerG T= in-3lane de5ormationG S= o(to5-3lane de5ormationG U= stretchin-G Vas= rocCingG Sas= twistingG V= ,endG n.a.= not assigned.

3.% !n #it$ cond$cti&ity mea#$rement# Ahe resisti8ity 8ers(s the a33lied electrode 3otential 3lot o5 PM* in !.& M A;*A4;Facetonitrile is dis3layed in 4ig(re &&a. PM* shows two changes in resisti8ity. Qhen the a33lied 3otential is increased' the resisti8ity o5 PM* decreases shar3ly ,y &." orders o5 magnit(de at !.& % and then increases again at !.#" %. Qhen the 3otential shi5t is re8ersed 5rom &.! to -!.2 %' the cond(cti8ity is almost com3letely restored. Ahe resisti8ity 8ers(s the a33lied electrode 3otential 3lot o5 the other homo3olymer' P<2$AC* in !.& M A;*A4;Facetonitrile is dis3layed in 4ig(re &&,. Ahe 3olymer shows a single change in resisti8ity. Qhen the a33lied 3otential is increased' the resisti8ity decreased shar3ly ,y 2.O orders o5 magnit(de aro(nd !.4" % with a highly sta,le cond(cti8ity (3 to &.2 %. In a 3otential scan ,acC 5rom &. to -!.2 %' the resisti8ity is almost com3letely restored. Ahe cond(cti8ity o5 P<2$AC* is aro(nd one order o5 magnit(de lower than that o5 3olythio3hene (%ogel B 1ol-e 2!! ). Ahe high resisti8ity o5 3olythio3hene as com3ared to that o5 P<2$AC* sho(ld ,e related the str(ct(ral di55erence ,etween them. Ahe 3resence o5 ethylenedio9y s(,stit(ents at the thio3hene ring in P<2$AC* increases the steric hindrance and distortion along the 3olymer chain which modi5ies the str(ct(re and th(s the 3ro3erties o5 the 3olymer. It sho(ld ,e mentioned that the o,ser8ed cond(cti8ity o5 PM* is less than that o5 P<2$AC* ,y 2.& orders o5 magnit(de.

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1.5

4ig(re &&. Resisti8ity 8ers(s electrode 3otential data in a sol(tion o5 acetonitrileK!.&M A;*A4; o5 (a) PM*' (,) P<2$AC*. In sit( cond(cti8ity meas(rements with di55erent monomers concentrations in the 3olymeri-ation sol(tion were 3er5ormedG res(lts o,tained with co3olymers o5 di55erent com3ositions are 3resented in 4ig(re. &2a-d. Ahe co3olymer C$P* (4ig(re. &2a) shows two change in resisti8ity. Qhen the a33lied 3otential is increased' the resisti8ity decreases shar3ly ,y 2.& orders o5 magnit(de at !.&: % with a sta,le resisti8ity (3 to !.O" % and then increases again. Ahe resisti8ity is almost com3letely restored when the 3otential is shi5ted ,acC 5rom &. to !.2 %. Ahe cond(cti8ity ,eha8ior o5 this co3olymer is 8ery close to that o5 PM* and less than that o5 P<2$AC ,y &.# orders o5 magnit(de. Ahis indicates that high M* (nits are incor3orated into the co3olymer chains. Ahe co3olymers C$P; (4ig(re. &2,) and C$PC (4ig(re. &2c) show two change in resisti8ity. Qhen the a33lied 3otential is increased' the resisti8ity decreases shar3ly ,y 2.2 orders o5 magnit(de at !.3O % in the case o5 C$P; and ,y2.# orders o5 magnit(de at !.4# % in the case o5 C$PC. Qith 5(rther increasing the a33lied 3otential ' the resisti8ity increased shar3ly at !.:: % in the case o5 C$P; and at !."# % in the case o5 C$PC. Ahe resisti8ity o5 C$P; and C$PC is not restored when the 3otential is re8ersed 5rom &. to -!.2 %. Ahis might ,e d(e to degradation o5 these co3olymers at high 3otentials. It was nota,le 5rom the 4ig(res &2, and c that the cond(cti8ity o5 the co3olymers C$P; and C$PC is higher than that o5 PM* and less than that o5 P<2$C*. Ahe cond(cti8ity o5 the C$P2 is o,ser8ed to ,e !.2 orders o5 magnit(de less than that o5 P<2$A. 4rom the 4ig(re &2d' the resisti8ity o5 C$P2 is decreases shar3ly ,y 2." orders o5 magnit(de at !.4: % and with 5(rther increasing the a33lied 3otential ' the resisti8ity increased at !." %. Ahe resisti8ity o5 this co3olymer is not restored when the 3otential is re8ersed 5rom &. to -!.2 %. ;ased on the o,ser8ations the in sit( cond(cti8ity ,eha8iors o5 the co3olymers are not the s(m o5 those o5 the two indi8id(al homo3olymers' ,(t seem to ,e determined ,y the <2$C* 5raction in the co3olymer. 4ig(re &3 re3resents the minim(m o,ser8ed resisti8ity o5 the homo3olymers and co3olymers 8ers(s mole 5raction o5 the <2$AC* that (sed in the 3olymeri-ation sol(tion. It was clearly that there is considera,le dro3 in o8erall resisti8ity e8en at the smallest <2$AC*-content.

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Chemistry and Materials Research ISSN 2224- 3224 (Print) ISSN 222 - !" # ($nline) %ol.3 No.&!' 2!&3

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6.0

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6.0 5.5

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A P O C

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R
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5.0 4.5 4.0 3.5 3.0 2.5 2.0

4.0

3.5

3.0 -0.5

0.0

0.5

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1.5

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0.0

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1.5

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6.5

6.5

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6.0 5.5

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C P O C
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g o L

3.5 3.0 2.5 2.0 -0.5 0.0 0.5 1.0 1.5

g o L

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5.0 4.5 4.0

m h o /

5.0 4.5 4.0 3.5 3.0 2.5 2.0 -0.5 0.0 0.5 1.0 1.5

4ig(re &2. Resisti8ity 8ers(s electrode 3otential data in a sol(tion o5 acetonitrileK!.&M A;*A4; o5 (a) C$$*' (,) C$P;' (c) C$PC' (d) C$P2. -( Conclusion Ahe electrochemical co3olymeri-ation o5 M* and <2$AC* was s(ccess5(lly reali-ed in a nona)(eo(s electrolytes . *t higher concentrations o5 M* in the 5eed' more M* (nits were incor3orated into the co3olymer. Ahe co3olymers showed 5airly good sta,ility. Ahe co3oly-mers 5ormed with di55erent 5eed concentrations o5 monomers e9hi,ited di55erent cyclic 8olt-ammetric ,eha8iors. *ll in sit( resisti8ities o5 the co3olymers were higher than that o5 PM* in less than that o5 P<2$AC* homo3olymers. Awo transitions were o,ser8ed in the in sit( con-d(cti8ities o5 the co3olymers. * dro3 in o8erall resisti8ity o5 the co3olymers was o,ser8ed e8en at the smallest <2$AC* content. *eferences $tero A. 4.' B Cantero I. (&"""). Cond(cting 3olymers as 3ositi8e electrodes in rechargea,le lithi(m-ion ,atteries. 'o$rnal of (o)er *o$rce#' :&N:2' :3:N:4& *manoC(ra /.' S(-(Ci X.' Ima,ayashi S.' B Qatana,e M. (2!!&). Poly3yrroleFPolymer <lectrolyte Com3osites Pre3ared ,y In Sit( <lectro3olymeri-ation o5 Pyrrole as CathodeF<lectrolyte Material 5or 4acile <lectron Arans5er at the Solid Inter5ace. 'o$rnal of The Electrochemical *ociety' &4:' 243-24:. D(r(nathan 6.' M(r(gan *. %.' Marim(th( R.' M(liC 7. P.' B *malnerCar 2. P. (&"""). <lectrochemically synthesised cond(cting 3olymeric materials 5or a33lications towards technology in electronics' o3toelectronics and energy storage de8ices. Material# Chemi#try and (hy#ic#' #&' &O3-&"& Mastragostino M.' *r,i--ani C.' B Soa8i 4. (2!!2). Cond(cting 3olymers as electrode materials in s(3erca3acitors. *olid *tate !onic#' &4:' 4"3N 4": D(3ta N.' Sharma S.' Mir I. *.' B 6(mar 2. (2!!#). *d8ances in sensors ,ased on cond(cting 3olymers. 'o$rnal of *cientific and !nd$#trial "e#earch' # ' 4"- O. Sot-ing D. *.' ;riglin S. M.' Dr(,,s R. 1.' B. Eewis N. S (2!!!). Pre3aration and Pro3erties o5 %a3or 2etector *rrays 4ormed 5rom Poly(3'4-ethylenedio9y)thio3heneYPoly(styrene s(l5onate)FIns(lating Polymer Com3o-sites. Analytical Chemi#try' O2' 3&:&N3&"! Ein C. Q.' 1wang ;. /.' B Eee C. R. (&"""). Characteristics and sensing ,eha8ior o5 electrochemically code3osited 3oly3yrroleN3oly(8inyl alcohol) thin 5ilm e93osed to ethanol 8a3ors. 'o$rnal of Applied (olymer

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Chemistry and Materials Research ISSN 2224- 3224 (Print) ISSN 222 - !" # ($nline) %ol.3 No.&!' 2!&3

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Chemistry and Materials Research ISSN 2224- 3224 (Print) ISSN 222 - !" # ($nline) %ol.3 No.&!' 2!&3

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Characteri#tic re2$encie# of Or,anic Molec$le#' ' New XorC= *cademic Press' Inc. EarCin P. (2!&&). !nfrared and "aman *pectro#copy4 (rinciple# and *pectral. New XorC= <lse8ier. St(art ;. (2!!4). !nfrared *pectro#copy4 $ndamental# and Application#. New XorC=Qiley.

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