Issue 6, 2012
From the journal:

Chemical Science

A complementary disk-shaped π electron donor–acceptor pair with high binding affinity†

Liana M. Klivansky,a   David Hanifi,a   Gayane Koshkakaryan,a   Daniel R. Holycross,b   Ewa K. Gorski,b   Qin Wu,c   Minghui Chai*b  and  Yi Liu*a  

* Corresponding authors

a The Molecular Foundry, Lawrence Berkeley National Laboratory, One Cyclotron Road, Berkeley, California, USA 94720
E-mail: yliu@lbl.gov

b Department of Chemistry, Central Michigan University, Mount Pleasant, Michigan, USA
E-mail: chai1m@cmich.edu

c Center for Functional Nanomaterials, Brookhaven National Laboratory, Upton, USA
E-mail: qinwu@bnl.gov

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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Article information

DOI
https://doi.org/10.1039/C2SC20241G
Article type
Edge Article
Submitted
26 Feb 2012
Accepted
30 Mar 2012
First published
03 Apr 2012

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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