Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene <i>S</i>,<i>S</i>-Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems

Verolet, Quentin; Soleimanpour, Saeideh; Fujisawa, Kaori; Dal Molin, Marta; Sakai, Naomi; Matile, Stefan

doi:10.1002/open.201402139

Scientific article

English

Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene S,S-Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems

Contributors

Verolet, Quentin; Soleimanpour, Saeideh; Fujisawa, Kaori; Dal Molin, Marta; Sakai, Naomi

; Matile, Stefan

Published in

ChemistryOpen, vol. 4, no. 3, p. 264-267

Publication date

2015

Abstract

Monomers with large surface area and high quantum yield, that is fluorescent flippers, have been engineered into twisted push–pull oligomers to create membrane probes with high mechanosensitivity and long fluorescence lifetime. Here, the synthesis and characterization of thieno[3,4]pyrazines and 2,1,3-benzothiadiazoles are described in comparison with the original dithienothiophene S,S-dioxides. Dithienothiophene S,S-dioxide flippers are confirmed as the best reported so far, and poor results with single flipper probes support that two flippers are needed for the probe to really “swim”, that is, for high mechanosensitivity.

Keywords

Fluorescent membrane probes
Mechanosensitivity
Oligomers
Push–pull fluorophores
Torsion angles
Twisted fluorophores

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VEROLET, Quentin et al. Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene S,S-Dioxides, Thieno[3,4]pyrazines and 2,1,3-Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems. In: ChemistryOpen, 2015, vol. 4, n° 3, p. 264–267. doi: 10.1002/open.201402139

Article (Published version)

Identifiers

PID : unige:73189
DOI : 10.1002/open.201402139

Journal ISSN

2191-1363

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325downloads

Creation

12/06/2015 11:28:00

First validation

12/06/2015 11:28:00

Update

13/10/2025 21:25:14

Status update

14/03/2023 23:22:34

Last indexation

16/02/2026 06:57:22