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Issue 6, 2012
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A complementary disk-shaped π electron donor–acceptor pair with high binding affinity

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Abstract

Hexaazatriphenylene triimides (HAT) have been shown to be a novel class of disk-shaped π electron acceptors that pair with donors with complementary shape and electron demands, such as triphenylene (TP) derivatives. The donor–acceptor (DA) pair forms a strong charge-transfer complex in CH2Cl2 with an association constant of 2.6 × 104 M−1, which is remarkable for a recognition system that is solely based on electrostatic interactions between two π systems. NMR studies, along with molecular modelling, have revealed a complementary charge distribution and an “eclipsed” conformation in the DA complex. The strong DA interaction results in extended alternating DA stacks in the thin film and mesophases.

Graphical abstract: A complementary disk-shaped π electron donor–acceptor pair with high binding affinity

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Publication details

The article was received on 26 Feb 2012, accepted on 30 Mar 2012 and first published on 03 Apr 2012


Article type: Edge Article
DOI: 10.1039/C2SC20241G
Citation: Chem. Sci., 2012,3, 2009-2014
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    A complementary disk-shaped π electron donor–acceptor pair with high binding affinity

    L. M. Klivansky, D. Hanifi, G. Koshkakaryan, D. R. Holycross, E. K. Gorski, Q. Wu, M. Chai and Y. Liu, Chem. Sci., 2012, 3, 2009
    DOI: 10.1039/C2SC20241G

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