Conducting polymers poly-3-alkylthiophenes

Yoshino, K., Nakano, K., Onoda, M., and Sugimoto, Ryu-ichi (1989) "Instability of conducting polymer, poly(3-alkylthiophene) gel with solvent, temperature and doping and effect of alkyl chain length". Solid State Commun. 70, 609-613. 

In the field of soluble conducting polymers new data have been published on poly(3-alkylthiophenes " l They show that the solubility of undoped polymers increases with increasing chain length of the substituent in the order n-butyl > ethyl methyl. But, on the other hand, it has turned out that in the doped state the electro-chemically synthesized polymers cannot be dissolved in reasonable concentrations In a very recent paper Feldhues et al. have reported that some poly(3-alkoxythio-phenes) electropolymerized under special experimental conditions are completely soluble in dipolar aprotic solvents in both the undoped and doped states. The molecular weights were determined in the undoped state by a combination of gel-permeation chromatography (GPC), mass spectroscopy and UV/VIS spectroscopy. It was established that the usual chain length of soluble poly(3-methoxthythiophene) consists of six monomer units. 

R.D. McCullough, R.D. Lowe, M. Jayaraman, and D.L. Anderson, Design, synthesis, and control of conducting polymer architectures structurally homogeneous poly(3-alkylthiophenes), J. Org. Chem., 58 904-912, 1993. 

Fig. 1 Building units of conducting polymers, (1) polyacetylene (PA) (2) polypyrrole (PPy), polythiophene (PTh), polyfurane (PFu) (3) polyphenylene (PP) (4) polyaniline (PANI) 5 polyindole (PIND) (6) polycarbazole (PCaz) (7) polyazulene (Paz) (8) polynaphthalene (PNa) (9) polyanthracene (PAnth) (10) polypyrene (PPyr) (11) polyfluorene (PFiu) (12) poly(isothionaphthalene) (PITN) (13) poly(dithienothiophene) (14) poly(thienopyrrole) (15) poly(dithienylbenzene) (1G) poly(3-alkylthiophene) (17) poly(phenylene vinylene) (18) poly(bipyrrole) (PBPy), poly(bithiophene) (PBT) (19) poly(phenylenesulfide) (20) 4-poly(thienothiophene) (21) poly(thienyl vinylene), poly(furane vinylene) (22) poly(ethylenedioxythiophene) (PEDOT).

The choice of counterion (anion or cation) has a major effect on the stability of conducting polymers. The stability of donor- (36) and acceptor-doped (37, 38) polyacetylenes, polypyrrole (39), poly(alkylthiophene)s (40), and other polymers (40) has been studied by using thermogravimetric anal-... 

FIGURE 6.9 Illustration of chain structure of poly(3-alkylthiophene) showing effect of head-head (HH) coupling in a mainly head-tail (HT) coupled chain. (From Jeffries-El, M. and McCullough, R.D., in Handbook of Conducting Polymers. Conjugated Polymers. Theory, Synthesis, Properties and Characterisation, 3rd edition, Skotheim, T.A. and Reynolds, J.R. (Eds.), CRC Press, Boca Raton, 2007, 9-1. With permission.)... 

McCullough, R.D. et al.. Self-orienting head-to-tail poly(3-alkylthiophenes) New insights on structure-property relationships in conducting polymers, J. Am. Chem. Soc. 115, 4910 911, 1993. 

EndrSdi, B., Melldr, J., Gingl, Z., Visy, C., Jandky, C., 2015. Molecular and supramolecular parameters dictating the thermoelectric performance of conducting polymers a case study using poly(3-alkylthiophene) s. J. Phys. Chem. C 119,8472-8479. 

McCullough, R.D. 1998. Regioregular, head-to-tail coupled poly(3-alkylthiophene) and its derivatives. In Handbook of conducting polymers, 2nd ed., eds. T.A. Skotheim, R.L. Elsenbaumer, J. R. Reynolds. NewYork Marcell Dekker, pp. 225-258. 

Bauerle, R, M. Hiller, S. Scheib, M. Sokolowski, and E. Umbach. 1996. Post-polymerization functionalization of conducting polymers Novel poly(alkylthiophene)s substituted with easily replaceable activated ester groups. Adv Mater 8 214-218. 

S. Oztemiz, G. Beaucage, O. Ceylan, H. B. Mark, Synthesis, characterization and molecular weight studies of certain soluble poly(3-alkylthiophene) conducting polymers, Journal of Solid State Electrochemistry 2004, 8, 928. 

---