Prev. Article Next Article Table of Contents

Article

Synthesis and Characterizations of Poly(9,10-bisarylethynyl-2,6-anthrylene)s and Poly(9,10-bisalkynyl-2,6-anthrylene)

Supporting Info

Weibin Cui†‡, Yun Zhao†‡, Hongkun Tian†, Zhiyuan Xie†, Yanhou Geng*† and Fosong Wang†

^† State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China

^‡ Graduate School of Chinese Academy of Sciences, Beijing 100049, P. R. China

Macromolecules, 2009, 42 (21), pp 8021–8027

DOI: 10.1021/ma901514q

Publication Date (Web): August 31, 2009

*Corresponding author. E-mail: yhgeng@ciac.jl.cn.

Abstract

A poly(9,10-bisalkynyl-2,6-anthrylene) (P1) and five poly(9,10-bisarylethynyl-2,6-anthrylene)s (P2−P6) as soluble conjugated polymers have been synthesized and characterized. All polymers exhibit two-dimensional conjugated characteristics as indicated by absorption spectra comprising multibands in the range of 300−600 nm. Compared with P1, polymers P2−P5, which contain phenylethynyl substituents with the longer conjugation than alkynyl groups, exhibit a 60 nm red shift of absorption edge. However, further increasing the conjugation length of the arylethynyl substituents (longer than phenylethynyl) has only a negligible effect on the conjugation of the polymer chains, while comparing the absorption spectra of P6 with those of P2−P5. All polymers show absorption spectra with a noticeable red shift from solutions to films, indicative of stronger intermolecular interaction in solid state. The highest occupied molecular orbital (HOMO) energy levels are −5.32 eV for P1 and around −5.20 eV for phenylethynyl-substituted polymers. Bulk heterojunction polymer solar cells (PSCs) of the polymers were fabricated with [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as the acceptor material. Polymer P1 exhibits the highest power conversion efficiency (PCE) of 1.60% with an open-circuit voltage (V_oc) of 0.96 V, a short-circuit current density (J_sc) of 3.18 mA/cm², and a fill factor (FF) of 0.53.