Cyclopenta-fused perylene: a new soluble, stable and functionalizable rylene building block

作     者：Wangdong Zeng Qingbiao Qi Jishan Wu 

作者机构：Department of Chemistry National University of Singapore Institute of Materials Research and Engineering 

出 版 物：《Science Bulletin》 (科学通报（英文版）)

年 卷 期：2015年第60卷第14期

页      面：1266-1271页

核心收录：

学科分类：081702[工学-化学工艺] 081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：supported by MOE Tier 2 Grant(MOE2011-T2-2-130) A*STAR-DST joint Grant(IMRE/14-2C0239) A*STAR JCO Grant(1431AFG100) 

主　　题：Organic dye Rylene Perylene Polycyclic aromatic hydrocarbon 

摘      要：We report a facile synthesis of a [l,12-b,c,d]- cyclopenta-fused perylene 5 from the parent perylene via a formylation-oxidative esterification-nucleophilic additionfollowed-by-Friedel-Crafts alkylation strategy. Compared with the perylene, dye 5 exhibits much higher solubility, smaller energy gap, and can undergo regio-selective bromination at the peri-positions. Compared with the N- annulated perylene 8, compound 5 shows lower HOMO energy level and is more stable in air. Therefore, 5 can be regarded a new versatile building block for the development of high-order soluble and stable rylenes and various perylene-based functional materials.