Issue 7, 2016

Supercoiled fibres of self-sorted donor–acceptor stacks: a turn-off/turn-on platform for sensing volatile aromatic compounds

Abstract

To ensure the comfortable survival of living organisms, detection of different life threatening volatile organic compounds (VOCs) such as biological metabolites and carcinogenic molecules is of prime importance. Herein, we report the use of supercoiled supramolecular polymeric fibres of self-sorted donor–acceptor molecules as “turn-off/turn-on” fluorescent sensors for the detection of carcinogenic VOCs. For this purpose, a C3-symmetrical donor molecule based on oligo(p-phenylenevinylene), C3OPV, and a perylene bisimide based acceptor molecule, C3PBI, have been synthesized. When these two molecules were mixed together in toluene, in contrast to the usual charge transfer (CT) stacking, supramolecular fibres of self-sorted stacks were formed at the molecular level, primarily driven by their distinct self-assembly pathways. However, CT interaction at the macroscopic level allows these fibres to bundle together to form supercoiled ropes. An interfacial photoinduced electron transfer (PET) process from the donor to the acceptor fibres leads to an initial fluorescence quenching, which could be modulated by exposure to strong donor or acceptor type VOCs to regenerate the respective fluorescence of the individual molecular stacks. Thus, strong donors could regenerate the green fluorescence of C3OPV stacks and strong acceptors could reactivate the red fluorescence of C3PBI stacks. These supercoiled supramolecular ropes of self-sorted donor–acceptor stacks provide a simple tool for the detection of donor- or acceptor-type VOCs of biological relevance, using a “turn-off/turn-on” fluorescence mechanism as demonstrated with o-toluidine, which has been reported as a lung cancer marker.

Graphical abstract: Supercoiled fibres of self-sorted donor–acceptor stacks: a turn-off/turn-on platform for sensing volatile aromatic compounds

Supplementary files

Article information

Article type
Edge Article
Submitted
10 feb 2016
Accepted
20 mar 2016
First published
21 mar 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 4460-4467

Author version available

Supercoiled fibres of self-sorted donor–acceptor stacks: a turn-off/turn-on platform for sensing volatile aromatic compounds

A. Sandeep, V. K. Praveen, K. K. Kartha, V. Karunakaran and A. Ajayaghosh, Chem. Sci., 2016, 7, 4460 DOI: 10.1039/C6SC00629A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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