Synthesis and properties of new small band gap conjugated polymers: methine bridged poly(3,4-ethylenedioxypyrrole)

ABSTRACT Synthesis and electronic properties of new small band gap conjugated polymers, methine-bridged poly(3,4-ethylenedioxy-pyrrole) (PEDOP) are reported. Density functional theory (B3LYP

with 6-31G basis) are used to obtain the optimized ground-state geometries and electronic structures of PEDOP and poly[(3,4-ethylenedioxypyrrole-2,5-diyl) methine] (PEDOP-M). Theoretical

bond length alternation of PEDOP is reduced by incorporating the methine bridge and leads to the band gap reduction from 2.44 to 0.68 eV. The small band gap characteristic of PEDOP-M is

further verified by preparing two conjugated polymers, poly[(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-benzylidene-(2,5-n-benzyl-3,4-ethylenedioxypyr-role-quinodimethanediyl)] (PBEDOP-B)

and poly[(2,5-n-benzyl-3,4-ethylenedioxypyrrolediyl)-(p-nitrobenzylidene)-(2,5-n-benzyl-3,4-ethylenedioxypyrrole-quinodimethanediyl)] (PBEDOP-NB). The optical band gap of PBEDOP-B and

PBEDOP-NB are 1.77 and 1.45 eV, respectively, while the electrochemical band gap of the former is 1.59 eV. Although the bulky side groups of these two polymers result in a larger band gap

than that of PEDOT-M, it indicates the small band gaps of such polymers. The nitrobenzene group could extend the π-conjugation and lead to the smaller band gap of PBEDOP-NB than that of

PBEDOP-B. The present study suggests that methine-bridged poly(3,4-ethylenedioxypyrrole) is a class of small band gap polymers. SIMILAR CONTENT BEING VIEWED BY OTHERS OXIDATIVE

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* Department of Chemical Engineering, National Taiwan University, Taipei, 106, Taiwan Jung-Hsun Tsai, Cheng-Liang Liu & Wen-Chang Chen * Institute of Polymer Science and Engineering,

National Taiwan University, Taipei, 106, Taiwan Wei-Ren Tu, Wen-Chung Wu & Wen-Chang Chen Authors * Jung-Hsun Tsai View author publications You can also search for this author inPubMed 

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Tsai, JH., Tu, WR., Liu, CL. _et al._ Synthesis and Properties of New Small Band Gap Conjugated Polymers: Methine Bridged Poly(3,4-ethylenedioxypyrrole). _Polym J_ 41, 363–369 (2009).

https://doi.org/10.1295/polymj.PJ2008263 Download citation * Received: 18 October 2008 * Accepted: 13 January 2009 * Published: 04 March 2009 * Issue Date: 01 May 2009 * DOI:

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currently available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing initiative KEYWORDS * Methine Bridged Polymers * Small Band Gap Polymers *

Poly(3,4-ethylenedioxypyrrole) * Density Functional Theory