While intramolecular Scholl oxidative coupling between two arenes is common, successful CÀ C heterocoupling between thiophene and arene is scarce. The latter is due to the notorious reactivity of thiophene towards polymerization under oxidative conditions. This report systematically demonstrates how topological variation of electronics and reactivity in thiophene substrates can lead to efficient oxidative heterocoupling. Bis(biaryl)thiophenes having reactive αand β-positions open are the choice of substrates. The cyclizing arene partners are so electronically tuned for thiophene's reactivity (at αand β-) as to establish CÀ C bond oxidatively generating symmetrical as well as unsymmetrical diphenanthrothiophenes which are basic thiananographenes. Depending on the cyclizing-couple's electronics, either areneor thiophene-centered oxidation initiates CÀ C heterocoupling. The potential utility of these simple thiananographenes is further unfurled by converting them to functional NÀ /Cgraphene segments that are aza-corannulene precursor and tetrabenzospirobifluorene. Their bright emission and extended electrochemical stability are remarkable that may be potentially important and applicable.
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