Limits...
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.

Verolet Q, Soleimanpour S, Fujisawa K, Dal Molin M, Sakai N, Matile S - ChemistryOpen (2015)

Bottom Line: 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.

View Article: PubMed Central - PubMed

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

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.

No MeSH data available.


Reagents and conditions: a) 1. nBuLi, THF, −78 °C, 20 min, 2. Bu3SnCl, THF, 15 h, rt, 61 %; b) 20, Pd(PPh3)4, DMF, 80 °C, 15 h, 38 % (22), 15 % (7′); c) 22, Pd(OAc)2, K2CO3, PEG4000, DMF, 120 °C, 5 h, 58 %.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4522174&req=5

sch03: Reagents and conditions: a) 1. nBuLi, THF, −78 °C, 20 min, 2. Bu3SnCl, THF, 15 h, rt, 61 %; b) 20, Pd(PPh3)4, DMF, 80 °C, 15 h, 38 % (22), 15 % (7′); c) 22, Pd(OAc)2, K2CO3, PEG4000, DMF, 120 °C, 5 h, 58 %.

Mentions: Oligomer 7 with 2,1,3-benzothiadiazole flippers was prepared from thiophene 19 (Scheme 3). Stille coupling between 20 and benzothiadiazole 21 gave monoester 22 and diester 7′.8 Final homocoupling of 22 gave the target molecule 7.


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.

Verolet Q, Soleimanpour S, Fujisawa K, Dal Molin M, Sakai N, Matile S - ChemistryOpen (2015)

Reagents and conditions: a) 1. nBuLi, THF, −78 °C, 20 min, 2. Bu3SnCl, THF, 15 h, rt, 61 %; b) 20, Pd(PPh3)4, DMF, 80 °C, 15 h, 38 % (22), 15 % (7′); c) 22, Pd(OAc)2, K2CO3, PEG4000, DMF, 120 °C, 5 h, 58 %.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4522174&req=5

sch03: Reagents and conditions: a) 1. nBuLi, THF, −78 °C, 20 min, 2. Bu3SnCl, THF, 15 h, rt, 61 %; b) 20, Pd(PPh3)4, DMF, 80 °C, 15 h, 38 % (22), 15 % (7′); c) 22, Pd(OAc)2, K2CO3, PEG4000, DMF, 120 °C, 5 h, 58 %.
Mentions: Oligomer 7 with 2,1,3-benzothiadiazole flippers was prepared from thiophene 19 (Scheme 3). Stille coupling between 20 and benzothiadiazole 21 gave monoester 22 and diester 7′.8 Final homocoupling of 22 gave the target molecule 7.

Bottom Line: 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.

View Article: PubMed Central - PubMed

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

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.

No MeSH data available.