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Issue 10, 2011
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Switching of non-helical overcrowded tetrabenzoheptafulvalene derivatives

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Abstract

This study explores a series of non-helical overcrowded tetrabenzoheptafulvalene derivatives, which are different from the parent tetrabenzoheptafulvalene (1) by avoiding terminal C–C double bonds, detailing their synthesis, characterization and syn/antiisomerization. The most interesting findings from this study are that the syn and anti isomers of three overcrowded tetrabenzoheptafulvalene derivatives (3–5) can be switched by photo- and thermal isomerizations both in very high yields. The predominance of syn isomer in the photoisomerization has been explained with DFT calculations in terms of the arrangement of the excited- and ground-state potential energy surfaces. The less stable syn isomer of an overcrowded tetrabenzoheptafulvalene derivative thermally isomerizes to the corresponding anti isomer through seven-membered ring flipping, and the energy barrier of thermal isomerization is found to be directly related to the rigidity and crowdedness of the seven-membered rings. These findings suggest that overcrowded tetrabenzoheptafulvalene derivatives are promising building blocks for molecular switches and machines. In addition, the new synthesis and unambiguous characterization of hexabenzoheptafulvalene (4) have also led to correction of the previously claimed synthesis of hexabenzooctalene.

Graphical abstract: Switching of non-helical overcrowded tetrabenzoheptafulvalene derivatives

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Publication details

The article was received on 01 Jun 2011, accepted on 05 Jul 2011 and first published on 21 Jul 2011


Article type: Edge Article
DOI: 10.1039/C1SC00340B
Chem. Sci., 2011,2, 2029-2034

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    Switching of non-helical overcrowded tetrabenzoheptafulvalene derivatives

    J. Luo, K. Song, F. L. Gu and Q. Miao, Chem. Sci., 2011, 2, 2029
    DOI: 10.1039/C1SC00340B

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