文献类型：期刊文献

英文题名：Aromatic Ring-Fused Dipyrrins: Programmed [4+2]-Cycloaddition Pathway with Regio-selectivity upon Alkylamino-Substitution

作者：Liu, Jiayang[1];Wang, Yuanyuan[1];Qiu, Ning[2];Liu, Xiujun[1];Li, Qizhao[1];Li, Yuxin[3];Wu, Xin-Yan[1];Li, Chengjie[1]

机构：[1]East China Univ Sci & Technol, Frontiers Sci Ctr Materiobiol & Dynam Chem, Shanghai Key Lab Funct Mat Chem, Sch Chem & Mol Engn,Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]Shanghai Starriver Bilingual Sch, Shanghai 201108, Peoples R China;[3]Heilongjiang Univ, Sch Chem & Mat Sci, Key Lab Funct Inorgan Mat Chem MOE, Harbin 150080, Peoples R China

年份：2023

卷号：88

期号：24

起止页码：17381

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20235115246360);WOS:【SCI-EXPANDED(收录号:WOS:001142957800001)】；

基金：This work was financially supported by the National Natural Science Foundation of China (22075077, 22131005, 22201074, and 22108078), the Natural Science Foundation of Shanghai (23ZR1415600 and 22ZR1416100), the Program of Shanghai Academic Research Leader (20XD1401400), the Shanghai Rising-Star Program (23QA1402100), and the Fundamental Research Funds for the Central Universities.

语种：英文

外文关键词：Aromatic compounds - Aromatization - Cycloaddition - Ketones - Olefins - Quinone

摘要：Sulfolenodipyrrins are employed as building blocks to concisely and efficiently construct aromatic rings (e.g., naphthoquinone, anthraquinone, fullerenes, and phthalimide) from fused dipyrrins by programmed [4 + 2]-cycloaddition reactions. Notably, alkylamino-substitution at the alpha-position not only enhances the reactivity of sulfolenodipyrrins but also results in the regio-selectivity of the cycloaddition reactions. Theoretical calculations in terms of frontier orbitals of dienes, energy of dienes, steric hindrance, and aromaticity have been conducted to understand the reason in depth. Additionally, the fusion of aromatic groups enables bathochromic absorption with up to similar to 130 nm for the monoadducts and to similar to 200 nm for the bis-adducts. The phthalimide annulation dipyrrin displays red emission, while the other mono- or bis-adducts do not, owing to the presence of typical acceptors such as quinone analogs or fullerene.