Synthesis and Characterization of Soluble and n-Dopable Poly(quinoxaline vinylene)s and Poly(pyridopyrazine vinylene)s with Relatively Small Band Gap

Abstract

Synthesis and characterization of poly(quinoxaline vinylene)s and poly(pyridopyrazine vinylene)s with linear and branched aliphatic side chains are reported. The electron affinity of the polymers was measured with cyclic voltammetry (CV) and found to be highest for the pyridopyrazine vinylene polymers. Compared to CN-MEH-PPV, the pyridopyrazine vinylene polymers were easier to reduce, while the quinoxaline derivatives were harder. UV-vis absorption measurements showed that the polymers have relatively small band gaps.

3,4‐Ethylenedioxythiophene–Pyridine‐Based Polymers: Redox or n‐Type Electronic Conductivity?

“…reduction to ±1.1 V. The increased acceptor strength allows for the insertion of a second electron per polymer repeat unit [16] 2 exhibits a second reduction process at ±1.6 V, the same potential as the reduction for 1. It is interesting to note that the reduction potential of 2 is about 100±200 mV more positive than those of the thiophene-based pyrido [3,4-b]pyrazine polymers [16] and pyrido [3,4-b]pyrazinevinylene polymers, [17] demonstrating the effect the donor has on the conduction band in relative energy space. In-situ conductance measurements of thin films on interdigitated microelectrodes show onsets of the doping processes consistent with that from cyclic voltammetry (Fig.…”

Electrochemical materials science: calculation vs. experiment as predictive tools in tailoring intrinsically conducting polythiophenes

“…The same observation has been made for other polythiophenes [172], poly(phenylene vinylene)s [173,174] and copolymers thereof [175], poly(quinoxaline vinylene)s and poly(pyridopyrazine vinylene) [176,177] and for fluorene-based copolymers [178]. Alternative evaluation of the optical bandgap is of course possible (absorption onset instead of absorption maximum: evaluation from photoluminescence spectra rather than absorption; optical absorption of polymer in solution rather than in film).…”

Conjugated copolymers of cyanosubstituted poly(p‐phenylene vinylene) with phenylene ethynylene and thienylene vinylene moieties: Synthesis, optical, and electrochemical properties

“…22 (b) The onset reduction potentials of P1, P2, and P3 occurred at about À1.33, À1.42, and À1.23 V versus Ag/Ag þ , respectively, which was greatly higher than that of MEH-PPV (À2.01 V) 17 and P3HT (À2.16 V). 22 (b) The results indicate that the three copolymers possessed high electron affinities, which could be attributed to the cyanosubstitution and the incorporation of triple bonds into the polymer main chains.…”

“…Conjugated polymers mostly possess a strong absorption band in the visible wavelength range, and their absorption band can be modified by a change in the polymer backbone or simply by the attachment of various side groups. [17][18][19] Currently, studies of photovoltaic conjugated polymers have mainly focused on the donor materials of the conjugated polymers. Li and coworkers [20][21][22][23][24] have synthesized a series of polythiophene and poly(thienylene vinylene) derivatives as donors with conjugated side chains for extending their absorption spectra to cover a broader wavelength range in the visible region.…”