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

ChemistryOpen

Quentin Verolet¹  Saeideh Soleimanpour¹  Dr. Kaori Fujisawa¹  Dr. Marta Dal Molin¹  Dr. Naomi Sakai¹ 

[1] Department of Organic Chemistry, University of Geneva, Geneva, Switzerland

关键词: fluorescent membrane probes;    mechanosensitivity;    oligomers;    push–pull fluorophores;    torsion angles;    twisted fluorophores;   

DOI  :  10.1002/open.201402139

来源: Wiley

【 摘 要 】

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.

【 授权许可】

CC BY-NC-ND   
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.