Issue 12, 2013

3,4-Ethylenedioxythiophene in planarizable push–pull oligothiophenes

Abstract

We report design, synthesis and evaluation of push–pull quaterthiophene amphiphiles containing one 3,4-ethylenedioxythiophene (EDOT) and a single strong twist in the scaffold. Planarizable push–pull oligothiophene amphiphiles have been introduced recently as conceptually innovative fluorescent probes that sense the fluidity and the potential of lipid bilayer membranes. The “hyper-twisted” EDOT probes respond to planarization and restricted rotational freedom with a red shift and changes in vibrational finestructure in the excitation spectrum, respectively. In solution, comparably weak solvatochromism and significant thermochromism are found. Planarization and restricted rotational freedom afford exquisite sensitivity toward nature and fluidity of lipid bilayer membranes, including ratiometric detection of phase transitions. The sensing of membrane potentials is weakened by these unique properties but remains possible.

Graphical abstract: 3,4-Ethylenedioxythiophene in planarizable push–pull oligothiophenes

Supplementary files

Article information

Article type
Paper
Submitted
20 Dec 2012
Accepted
23 Jan 2013
First published
07 Feb 2013

Org. Biomol. Chem., 2013,11, 1952-1957

3,4-Ethylenedioxythiophene in planarizable push–pull oligothiophenes

M. Dal Molin and S. Matile, Org. Biomol. Chem., 2013, 11, 1952 DOI: 10.1039/C3OB27471C

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