期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 18, 页码 8394-8405出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01573
关键词
-
资金
- Bavarian Research Program Solar Technologies Go Hybrid
- Fonds der Chemischen Industrie
Here, we present a collection of different azabenz-annulated perylene derivatives. By developing new synthetic strategies and improving existing protocols, we have expanded the structural diversity of these dye molecules to a multifunctional class of ligating chromophores. The Pictet Spengler (PS) reaction of 1-aminoperylenes with different aldehydes is used to modify the terminal substitution pattern. PS transformations of 1,6- and/or 1,7-diamino perylenes result in 2-fold annulated nitrogen-containing coronene-type molecules like anti-(ab)(2)-PBI 15, syn(ab)(2)-PB1 16, and syn-(ab)(2)-PTE 18. In addition, azabenz-annulated perylene bisanhydrides (ab-PBA 6 and syn-(ab)(2)-PBA 19) were explored as universal starting materials providing access to any desired imide functionality. Furthermore, a newly developed regioselective nitration procedure for perylene monoimide diesters (PMIDE) enables the synthesis of 1-nitro-PMIDE 10 and thus of azabenz-annulated perylene derivatives with unsymmetric peri-substitution patterns (ab-PMIDE 12 and ab-PMIMA 13). According to our spectroscopic and theoretical investigations, the optical and electrochemical properties of these multifunctional chromophores can easily be modified and adjusted to many desirable applications following the synthetic strategies presented in this work.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据