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The syntheses of naphtho[2,3-b:7,6-b′]- and naphtho[2,1-b:5,6-b′]bisbenzo[b]thiophenes (NBBTs) are achieved via inter- and intramolecular stepwise Friedel–Crafts-type reactions. The structural curvature of these NBBTs are found to improve their solubility in organic solvents, and to form well-defined herringbone structures in single crystals, especially when the C 2v symmetrical naphtho[2,3-b:7,6-b′]bisbenzo[b]thiophene...
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