Synthesis of quinoxaline-benzoxale conjugates and mesomorphic properties

Chun Jung Chen, Yu Che Wu, Hwo Shuenn Sheu, Gene Hsiang Lee, Chung K. Lai

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Abstract

A new series of non-discotic heterocyclic compounds 1a-e derived from quinoxaline was prepared and their mesomorphic properties investigated. The crystal and molecular structures of nonmesogenic 2,3-bis(3,4-didodecyloxyphenyl) quinoxaline-6-carboxylic acid 4-[(4-butoxy2-hydroxyphenylimino)methyl]phenyl ester 2a (n=4, m=12) were determined by means of X-ray structural analysis. It crystallizes in a monoclinic space group P2(1)/c, with a=21.9193(13) , b=8.3693(4) , c=30.896(2) , and Z=4. The molecule was considered as an elongated or tapered triangle. Both inter- and intra-molecular H-bonds were observed in the crystal lattice, which was attributed to the formation of columnar mesophase in compounds 2. The mesomorphic behavior of compounds 1-2 was studied by thermal analysis and polarized optical microscopy. All compounds 1-2 exhibited hexagonal columnar phases (Colh), which were also confirmed by powder XRD diffractometer. A Ncell and Rar value equal to 4.74 and 4.34 within a slice of 9.0 thick were obtained for 1b and 2b, indicating that a more disc-like correlated structure by two molecules lying side-by-side was formed in Colh phases. The fluorescent properties of the compounds 1-4 in CH3Cl were also examined.

Original languageEnglish
Pages (from-to)114-124
Number of pages11
JournalTetrahedron
Volume67
Issue number1
DOIs
StatePublished - 7 Jan 2011

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