Embedding 1,6-Diphenyl-1,2-Dihydronaphthalene (DHN) in 1,4-Distyrylbenzene (DSB): Arene-Arene Interactions in a "Crossed Bis-Diarene"
The C38H32 hydrocarbon 1-methyl-1,3,6-triphenyl-7- [(E)-2-phenyl-propenyl]-1,2-dihydronaphthalene (I) presents a novel framework that combines the functionalities of a 1,6-diarene-substituted 1,2-dihydronaphthalene (DHN) with a 1,4-distyrylbenzene (DSB). The hydrocarbon was synthesized, the crystal structure of (±)-I was determined, and a detailed analysis of intermolecular interactions is presented. The crossed bis-diarene I has the capability to engage in arene-arene interactions in two nearly orthogonal directions, and various types of arene-arene interactions cooperate in the formation of its lamellar crystal architecture. While the DSB units alternate within both the R- and the S-substructures, the homochiral substructures feature opposing polarity along the long axes of the DHN-based diarenes, and hence the possibility exists for polar quasiracemic crystals. Importantly, the analysis of arene-arene contacts provides strong evidence that chemical modifications of the arenes attached to the DHN unit are possible without fundamental impediments of the lattice architecture.
Y. Sui and R. Glaser, "Embedding 1,6-Diphenyl-1,2-Dihydronaphthalene (DHN) in 1,4-Distyrylbenzene (DSB): Arene-Arene Interactions in a "Crossed Bis-Diarene"," Crystal Growth and Design, vol. 6, no. 4, pp. 1014-1021, American Chemical Society (ACS), Mar 2006.
The definitive version is available at https://doi.org/10.1021/cg0506626
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