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 |
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| Authors: | Quentin Verolet Saeideh Soleimanpour Dr Kaori Fujisawa Dr Marta Dal?Molin Dr Naomi Sakai Prof Stefan Matile |
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| Institution: | aDepartment of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211, Geneva, Switzerland |
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| 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 thieno3,4]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. |
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| Keywords: | fluorescent membrane probes mechanosensitivity oligomers push– pull fluorophores torsion angles twisted fluorophores |
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