Synthesis of Thiophene 1,1-Dioxides and Tuning Their Optoelectronic Properties

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• 作者：Chia-Hua Tsai ; Danielle N. Chirdon ; Andrew B. Maurer ; Stefan Bernhard ; Kevin J. T. Noonan
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：October 18, 2013
• 年：2013
• 卷：15
• 期：20
• 页码：5230-5233
• 全文大小：263K
• 年卷期：v.15,no.20(October 18, 2013)
• ISSN：1523-7052

文摘

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 鈥揅₆H₄-p-NO₂ substituents produce a 510 mV shift as compared to a thiophene 1,1-dioxide with two phenyl groups.