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Towards the Highly Efficient Synthesis and Selective Methylation of C(sp3)‐Bridged [6]Cycloparaphenylenes from Fluoren[3]arenes.
- Source :
- Angewandte Chemie; 6/1/2021, Vol. 133 Issue 23, p13131-13138, 8p
- Publication Year :
- 2021
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 133
- Issue :
- 23
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 150516072
- Full Text :
- https://doi.org/10.1002/ange.202102701