Issue 24, 2016

Light-triggered assembly–disassembly of an ordered donor–acceptor π-stack using a photoresponsive dimethyldihydropyrene π-switch

Abstract

Self-organization of donor and acceptor π-systems forms alternate D–A stacks of the donor and acceptor molecules. Using a photochromic π-switch as a donor and an electron deficient acceptor dye such stacks were formed. Photomodulation of the donor unit with visible light led to a photoisomerized state having a non-planar structure with reduced donor ability, thereby causing destruction of the alternate D–A π-stacks. The formation and destruction of the stacks were studied by various spectroscopy methods. Both the stacks and the depleted stacks were studied by DLS and SEM experiments. The regeneration of the stacks occurred in solution with the reversal of the photoisomerization process with ultraviolet light. Computational and differential scanning calorimetric studies validated the thermodynamics of the formation of the stacks. This work presents a reversible assembly–disassembly of a donor–acceptor π system devoid of additional auxiliary non-covalent bonding motifs in the donor and acceptor molecules.

Graphical abstract: Light-triggered assembly–disassembly of an ordered donor–acceptor π-stack using a photoresponsive dimethyldihydropyrene π-switch

  • This article is part of the themed collection: New Talent

Supplementary files

Article information

Article type
Paper
Submitted
14 Jan 2016
Accepted
15 Feb 2016
First published
22 Feb 2016

Org. Biomol. Chem., 2016,14, 5744-5750

Light-triggered assembly–disassembly of an ordered donor–acceptor π-stack using a photoresponsive dimethyldihydropyrene π-switch

V. S. R. Krishna, M. Samanta, S. Pal, N. P. Anurag and S. Bandyopadhyay, Org. Biomol. Chem., 2016, 14, 5744 DOI: 10.1039/C6OB00101G

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