BODIPY-Based Donor鈥揂cceptor 蟺-Conjugated Alternating Copolymers

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• 作者：Bhooshan C. Popere ; Andrea M. Della Pelle ; S. Thayumanavan
• 刊名：Macromolecules
• 出版年：2011
• 出版时间：June 28, 2011
• 年：2011
• 卷：44
• 期：12
• 页码：4767-4776
• 全文大小：1063K
• 年卷期：v.44,no.12(June 28, 2011)
• ISSN：1520-5835

文摘

Four novel 蟺-conjugated copolymers incorporating 4,4-difluoro-4-borata-3a-azonia-4a-aza-s-indacene (BODIPY) core as the 鈥渄onor鈥?and quinoxaline (Qx), 2,1,3-benzothiadiazole (BzT), N,N鈥?di(2鈥?ethyl)hexyl-3,4,7,8-naphthalenetetracarboxylic diimide (NDI), and N,N鈥?di(2鈥?ethyl)hexyl-3,4,9,10-perylene tetracarboxylic diimide (PDI) as acceptors were designed and synthesized via Sonogashira polymerization. The polymers were characterized by ¹H NMR spectroscopy, gel permeation chromatography (GPC), UV鈥搗is absorption spectroscopy, and cyclic voltammetry. Density functional theory (DFT) calculations were performed on polymer repeat units, and the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels were estimated from the optimized geometry using B3LYP functional and 6-311g(d,p) basis set. Copolymers with Qx and BzT possessed HOMO and LUMO energy levels comparable to those of BODIPY homopolymer, while PDI stabilized both HOMO and LUMO levels. Semiconductor behavior of these polymers was estimated in organic thin-film transistors (OTFT). While the homopolymer, Qx, and BzT-based copolymers showed only p-type semiconductor behavior, copolymers with PDI and NDI showed only n-type behavior.