New Form of an Old Natural Dye: Bay-Annulated Indigo (BAI) as an Excellent Electron Accepting Unit for High Performance Organic Semiconductors

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• 作者：Bo He ; Andrew B. Pun ; Danylo Zherebetskyy ; Yao Liu ; Feng Liu ; Liana M. Klivansky ; Alexandra M. McGough ; Benjamin A. Zhang ; Kelvin Lo ; Thomas P. Russell ; Linwang Wang ; Yi Liu
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：October 22, 2014
• 年：2014
• 卷：136
• 期：42
• 页码：15093-15101
• 全文大小：704K
• ISSN：1520-5126

文摘

A novel electron acceptor was synthesized from one-step functionalization of the readily available indigo dye. The resulting bay-annulated indigo (BAI) was utilized for the preparation of a series of novel donor鈥揳cceptor small molecules and polymers. As revealed experimentally and by theoretical calculations, substituted BAIs have stronger electron accepting characteristics when compared to several premier electron deficient building blocks. As a result, the donor鈥揳cceptor materials incorporating BAI acceptor possess low-lying LUMO energy levels and small HOMO鈥揕UMO gaps. In situ grazing incidence wide-angle X-ray scattering studies of the thin films of BAI donor鈥揳cceptor polymers indicated improved crystallinity upon thermal treatment. Field effect transistors based on these polymers show excellent ambipolar transporting behavior, with the hole and electron mobilities reaching 1.5 and 0.41 cm² V^鈥? s^鈥?, respectively, affirming BAI as a potent electron accepting unit for high performance organic electronic materials.