title: 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.
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.
authors.affiliation: Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30, 1211, Geneva, Switzerland.
authors.forename: Quentin
authors.initials: Q
authors.lastname: Verolet
authors.affiliation: Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30, 1211, Geneva, Switzerland.
authors.forename: Saeideh
authors.initials: S
authors.lastname: Soleimanpour
authors.affiliation: Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30, 1211, Geneva, Switzerland.
authors.forename: Kaori
authors.initials: K
authors.lastname: Fujisawa
authors.affiliation: Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30, 1211, Geneva, Switzerland.
authors.forename: Marta
authors.initials: M
authors.lastname: Dal Molin
authors.affiliation: Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30, 1211, Geneva, Switzerland.
authors.forename: Naomi
authors.initials: N
authors.lastname: Sakai
authors.affiliation: Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30, 1211, Geneva, Switzerland.
authors.forename: Stefan
authors.initials: S
authors.lastname: Matile
keywords: fluorescent membrane probes; mechanosensitivity; oligomers; push–pull fluorophores; torsion angles; twisted fluorophores