EDOP

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Alternation of electron-rich and poor units in conjugated systems is expected to reduce the handgap due to the concomitant increase of HOMO level and decrease of LUMO level. Hence the use of stronger donor units, such as EDOT [92] and 3,4-ethylenedioxypyrrole (EDOP) [93], in PTV-like structure 28 and 29, respectively, allowed a further decrease of the gap to 1.1-1.2 eV. Recently, following the same approach a soluble narrow handgap polymer 30 (Eg =1.7 eV) was described by Reynolds and coworkers... 

Thus, Cava et al. have synthesized 3,4-ethylenedioxyselenophene (EDOS) [133]. Poly(alkylenediox-yfuran)s such as poly(EDOF) have been developed as photothermographic image-forming materials [134]. EDOP was first synthesized in 1995 by Merz et al. [135]. Recently, this monomer and its analogs, ProDOP and BuDOP, have been intensively investigated by Reynolds and coworkers and considered in relation with their potential applications in biosensors [136,137]. 

About 15 years ago was published the unequivocal demonstration of the fact that the first steps of the polymerization of pyrrole and several pyrrole derivatives in dry acetonitrile were the coupling of cation-radicals [6,133]. Further studies by Hapiot and Audebert have shown that this could be extended to several types of thiophene [134] and pyrrole oligomers [98,135], from four to six units length. It has been assumed since then (and even before) that this was the same for all heterocycles, although the study of thiophene itself is impossible (the cation-radical is far too much unstable), as well as bithiophene and terthiophene, whose cation radicals are also too much reactive. This is also unfortunately the case of EDOT and its pyrrole analog EDOP, although the lifetime of the cation radical of EDOP could be recently estimated in particular conditions [136]. 

Ethylenedioxypyrrole (EDOP, 2) and Propylenedioxypyrrole (PRODOP, 3) are synthesized from dimethyl-3,4-dihydroxypyrrole-2,5-dicarboxylate in five... 

Chart 11.1 4-(pyrrol-l-yl-ethyl)pyridine (1), EDOP (2) and ProDOP (3). 

The first synthesis of a 3,4-dialkoxypyrrole (3,4-dimethoxypyrrole) was published by Merz et al. The EDOT analog3,4-ethylenedioxypyrrole (EDOP) soon followed,and its poly(styrenesulfonic acid) complex PEDOPrPSS analog to PEDOT PSS was claimed in a patent 1996. ... 

The synthetic routes to the monomeric EDOP and similar compounds are roughly outlined in Pigure 13.21, following the Reynolds and Walczak review, where more detailed comments can be found. ... 

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