Embedding 1,6-Diphenyl-1,2-Dihydronaphthalene (DHN) in 1,4-Distyrylbenzene (DSB): Arene-Arene Interactions in a "Crossed Bis-Diarene"

Author

Yongqiang Sui
Rainer Glaser, Missouri University of Science and TechnologyFollow

Abstract

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.

Recommended Citation

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

Department(s)

Chemistry

International Standard Serial Number (ISSN)

1528-7483; 1528-7505

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2006 American Chemical Society (ACS), All rights reserved.

Publication Date

01 Mar 2006