期刊
CHEMICAL SCIENCE
卷 2, 期 8, 页码 1480-1486出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00156f
关键词
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资金
- US Department of Energy, Office of Basic Energy Sciences [DE-SC0001085]
- National Science Foundation [CHE0936923]
- Center on Functional Engineered Nano Architectonics (FENA) [2009-NT-2048]
We detail a general method for the synthesis of dibenzotetrathienocoronenes and elucidate their solid state structures in crystals and co-crystals. The contorted dibenzotetrathienocoronene (c-DBTTC) is a tetrathiophene-fused version of the previously studied contorted hexabenzocoronenes (c-HBC). The synthesis detailed here is simple and provides easy access to this important class of materials. We have found that these materials display molecular flexibility and tunable supramolecular self-assembly properties in the solid state by shifting molecular conformations between two different conformations. Depending on the conditions under which a c-DBTTC-containing material crystallizes, the c-DBTTC adopts either the up-down or the butterfly conformation. When grown from the vapor phase, crystals of the unsubstituted c-DBTTC show the molecule only in the up-down conformation, and it packs into dense crystals containing columnar arrays with close intracolumnar packing. The packing is controlled by the inherent molecular corrugation of the three-dimensional core and sulfur-sulfur interactions. When grown as co-crystals with electron acceptors from solution, the butyl-substituted c-DBTTC either adopts the butterfly conformation when the electron acceptor is small enough to be completely enveloped (TCNQ) or the up-down conformation when the electron acceptor is relatively large (C(60)). When grown from organic solvent crystals of the butyl-substituted c-DBTTC contain molecules of the solvent as the only guest, and we observe both conformations of the c-DBTTC. Controlling the supramolecular structure is the key to developing these materials for electronic applications.
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