Towards the Highly Efficient Synthesis and Selective Methylation of C(sp 3 )‐Bridged [6]Cycloparaphenylenes from Fluoren[3]arenes

Autor:	Da-Wei Zhang, Jing Li, Xu-Sheng Du, Yan Guo, Chuan-Feng Chen, Ying Han
Rok vydání:	2021
Předmět:	010405 organic chemistry Chemistry Stereochemistry Band gap General Chemistry Crystal structure Methylation General Medicine 010402 general chemistry 01 natural sciences Fluorescence Catalysis Coupling reaction 0104 chemical sciences Intramolecular force Demethylation
Zdroj:	Angewandte Chemie. 133:13131-13138
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.202102701
Popis:	An approach to the highly efficient synthesis of C(sp3)-bridged [6]cycloparaphenylenes (C[6]CPPs) from fluoren[3]arenes (F[3]As) was developed. Consequently, F[3]As as a new kind of macrocyclic arenes were synthesized. Followed by the demethylation, triflation and intramolecular aryl-aryl coupling reactions, C[6]CPPs were then conveniently obtained. Interestingly, C[6]CPPs could be selectively methylated to produce their fully outer-methyl-substituted derivatives. The crystal structures showed the hydroxyl-substituted F[3]As had bowl-shaped conformations, and the C[6]CPPs exhibited rigid belt-shaped structures with deep cavities. Moreover, C[6]CPPs exhibited high HOMO energies and narrow energy gaps. An unclosed belt was further obtained, and it not only showed a similar narrow energy gap to those of the aromatic belts, but also displayed strong fluorescence property, which can play a vital role in the design and synthesis of new aromatic belts.
Databáze:	OpenAIRE
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