Symmetrical mesogenic 2,5-bis(6-naphthalen-2-yl)-1,3,4-thiadiazoles

Hsiu Ming Kuo, Sih Yeh Li, Hwo Shuenn Sheu, Chung K. Lai

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

Two series of new symmetrical 1,3,4-oxadiazoles 1a-n and 1,3,4-thiadiazoles 1b-n were prepared and their mesomorphic properties investigated by optical microscopy, differential scanning calorimetry, and powder X-ray diffractometry. Compounds 1b-n are kinetically more stable than compounds 1a-n. Compounds 1a-n exhibited monotropic nematic or smectic C phases, whereas, compounds 1b-n exhibited enantiotropic nematic or smectic A/smectic C phases. Compounds 1b-n have higher clearing temperatures and the larger temperature ranges of mesophases, which might be attributed to the better linearity and/or larger dipole, resulted from a more polarized sulfur atom than oxygen atom incorporated. The fluorescent properties of these two series of 1,3,4-thiadiazole/oxadiazole-based derivatives were also examined. The λ max peaks of the photoluminescence spectra for compounds 1a-6 and 1b-6 measured in THF occurred at ca. 385 nm and 423 nm, respectively. Both series were blue emitters.

Original languageEnglish
Pages (from-to)7331-7337
Number of pages7
JournalTetrahedron
Volume68
Issue number36
DOIs
StatePublished - 9 Sep 2012

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