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Verolet Q, Soleimanpour S, Fujisawa K, 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. ChemistryOpen. 2015;4(3):264-7doi: 10.1002/open.201402139.
Verolet, Q., Soleimanpour, S., Fujisawa, K., Dal Molin, M., Sakai, N., & Matile, S. (2015). 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, 4(3), 264-7. https://doi.org/10.1002/open.201402139
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." ChemistryOpen vol. 4,3 (2015): 264-7. doi: https://doi.org/10.1002/open.201402139
Verolet Q, Soleimanpour S, Fujisawa K, Dal Molin M, Sakai N, Matile S. 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. 2015 Jun;4(3):264-7. doi: 10.1002/open.201402139. Epub 2015 Feb 05. PMID: 26246986; PMCID: PMC4522174.
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ChemistryOpen. 2015 Jun;4(3):264-7. doi: 10.1002/open.201402139. Epub 2015 Feb 05.

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

Affiliations

  1. Department of Organic Chemistry, University of Geneva Quai Ernest Ansermet 30, 1211, Geneva, Switzerland.

PMID: 26246986 PMCID: PMC4522174 DOI: 10.1002/open.201402139

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

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