Microwave synthesis and fluorous purification of 4-(tetrathienyl)butyric acid for self-assembled monolayer semiconductor applications |
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Authors: | Mark C. McCairn |
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Affiliation: | School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, United Kingdom |
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Abstract: | Microwave-promoted synthesis and fluorous purification procedures have been employed successfully to generate 4-(tetrathienyl)butyric acid rapidly. Initially, a fluorous tag 1H,1H-perfluorooctylamine was tethered to 4-(thienyl)butyric acid via an amide traceless linkage. Subsequent, sequential α-bromination and Stille cross-coupling reactions with 2-(tributylstannyl)thiophene grew the fluorous-tagged 4-(oligothienyl)butyric acid efficiently. Each synthetic transformation was followed by a fluorous-solid phase extraction procedure to isolate the fluorous-tagged compound intermediate in excellent yield. Finally, the fluorous tag was cleaved by microwave-promoted saponification of the amide bond to liberate the desired 4-(tetrathienyl)butyric acid. |
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Keywords: | Self-assembled monolayer Traceless fluorous tag Organic semiconductor |
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