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

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• 作者：Wangdong Zeng ; Qingbiao Qi ; Jishan Wu
• 关键词：Organic dye ; Rylene ; Perylene ; Polycyclic aromatic hydrocarbon
• 刊名：Chinese Science Bulletin
• 出版年：2015
• 出版时间：July 2015
• 年：2015
• 卷：60
• 期：14
• 页码：1266-1271
• 全文大小：758 KB
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• 作者单位：Wangdong Zeng (1)
  Qingbiao Qi (1)
  Jishan Wu (1) (2)
  
  1. Department of Chemistry, National University of Singapore, Singapore, 117543, Singapore
  2. Institute of Materials Research and Engineering, A*STAR, Singapore, 117602, Singapore
  
• 刊物主题：Science, general; Life Sciences, general; Physics, general; Chemistry/Food Science, general; Earth Sciences, general; Engineering, general;
• 出版者：Springer Berlin Heidelberg
• ISSN：1861-9541

文摘

We report a facile synthesis of a [1,12-b,c,d]cyclopenta-fused perylene 5 from the parent perylene via a formylation-oxidative esterification–nucleophilic addition-followed-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.