Scientific article
OA Policy
English

Mechanosensitive Oligodithienothiophenes: Transmembrane Anion Transport Along Chalcogen-Bonding Cascades

Published inHelvetica Chimica Acta, vol. 101, no. 4, e1800014
Publication date2018
Abstract

The design, synthesis, and evaluation of multifunctional dithieno[3,2‐b;2′,3′‐d]thiophene (DTT) trimers is described. Twisted push‐push‐pull or donor‐donor‐acceptor (DDA) trimers composed of one DTT acceptor and two DTT donors show strong mechanochromism in lipid bilayer membranes. Red shifts in excitation rather than emission and fluorescence recovery with increasing membrane order are consistent with planarization of the twisted, extra‐long mechanophores in the ground state. The complementary pull‐pull‐pull or AAA trimers with deep σ holes all along the scaffold are not mechanochromic in membranes but excel with submicromolar anion transport activity. Anion transport along membrane‐spanning strings of chalcogen‐bond donors is unprecedented and completes previous results on transmembrane cascades that operate with equally unorthodox interactions such as halogen bonds and anion‐π interactions.

Citation (ISO format)
MACCHIONE, Mariano et al. Mechanosensitive Oligodithienothiophenes: Transmembrane Anion Transport Along Chalcogen-Bonding Cascades. In: Helvetica Chimica Acta, 2018, vol. 101, n° 4, p. e1800014. doi: 10.1002/hlca.201800014
Main files (1)
Article (Published version)
Identifiers
Journal ISSN0018-019X
581views
204downloads

Technical informations

Creation04/23/2018 2:41:00 PM
First validation04/23/2018 2:41:00 PM
Update time03/15/2023 8:09:38 AM
Status update03/15/2023 8:09:37 AM
Last indexation10/31/2024 10:07:29 AM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack