Liquid crystalline radicals: discotic behavior of unsymmetrical derivatives of 1,3,5-triphenyl-6-oxoverdazyl
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A series of six 6-oxoverdazyl (1) substituted with a total of three 3,4,5-tri(decyloxy)phenyl and/or 3,4,5-tri(decylsulfanyl)phenyl groups was investigated by thermal, XRD, spectroscopic, magnetic and photovoltaic methods. The compounds exhibit columnar hexagonal (1c, Colh), columnar hexagonal ordered (1b, Colh(o)), columnar hexagonal 3D (1a, 1e and 1f, Colh(3D)) or a sequence of two phases (1b, Colh–Colh(3D)). The mesophase structure and stability and also thermochromism were investigated as a function of the number and distribution of decyloxy and decylsulfanyl substituents in the molecule. Thermal analysis demonstrated that the presence of the 3,4,5-tri(decyloxy)phenyl substituent in the C(3) position increases the phase stability. Spectroscopic analysis showed that only all-decyloxy derivative 1b exhibits a hypsochromic shift upon Colh(o) formation, while all other compounds in the series show a modest bathochromic shift in the columnar phase relative to the isotropic phase. Magnetization investigation of 1d demonstrated the paramagnetic behavior of isolated spins in isotropic and columnar phases. Negligible photocurrent was detected for 1d in the columnar phase.
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