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Synthesis of thiophene 1,1-dioxides and tuning their optoelectronic properties. 2013

Chia-Hua Tsai, and Danielle N Chirdon, and Andrew B Maurer, and Stefan Bernhard, and Kevin J T Noonan
Department of Chemistry, Carnegie Mellon University , 4400 Fifth Avenue, Pittsburgh , Pennsylvania, 15213, United States.

A 2,5-bis(tributylstannyl)thiophene 1,1-dioxide was prepared from 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide, bis(tributyltin) oxide, and tetrabutylammonium fluoride (TBAF). The 2,5-bis(tributylstannyl)thiophene 1,1-dioxide and a 2,5-diiodothiophene 1,1-dioxide were utilized in a series of Stille cross-coupling reactions to afford thiophene 1,1-dioxides with either electron-donating or electron-withdrawing substituents. Electron-withdrawing groups greatly facilitate the reduction of these sulfone heterocycles, and -C6H4-p-NO2 substituents produce a 510 mV shift as compared to a thiophene 1,1-dioxide with two phenyl groups.

UI MeSH Term Description Entries
D009947 Organotin Compounds Organic compounds which contain tin in the molecule. Used widely in industry and agriculture. Compounds, Organotin
D013876 Thiophenes A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur. Thiophene
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D055664 Electrochemical Techniques The utilization of an electrical current to measure, analyze, or alter chemicals or chemical reactions in solution, cells, or tissues. Electrochemical Technics,Electrochemical Technic,Electrochemical Technique,Technic, Electrochemical,Technics, Electrochemical,Technique, Electrochemical,Techniques, Electrochemical

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