Chiral photochromic 2-(N-acyl-N-arylaminomethylene)benzo[b]thiophen-3(2H )-ones

Author： Rybalkin V.P.   Shepelenko E.N.   Vorob'eva Y.Y.   Borodkin G.S.   Bren' V.A.   Minkin V.I.   Aldoshin S.M.   Tkachev V.V.   Utenyshev A.N.  

Publisher： Springer Publishing Company

ISSN： 1066-5285

Source： Russian Chemical Bulletin, Vol.52, Iss.8, 2003-08, pp. : 1800-1806

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Abstract

Photochromic 2-(N-acyl-N-arylaminomethylene)benzo[b]thiophen-3(2H )-ones containing ortho-substituents in the N-phenyl ring were studied by X-ray diffraction analysis and 1H NMR spectroscopy. It was established that these compounds have stable chiral structures due to hindered rotation of the phenyl ring around the C—N bond. The energy barrier to racemization evaluated by dynamic NMR spectroscopy is ΔG#428 K = 98 kJ mol–1.

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