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Novel Bisstyryl Dyes Containing 18-crown-6 moieties: Synthesis, Complexation with Ammonium Substrates and [2+2]-photocycloaddition

Dmitry V. Kondratuk ,  Natalia A. Lobova ,  Evgeny N. Ushakov ,  Artem I. Vedernikov ,  Michael V. Alfimov ,  Sergey P. Gromov 

Photochemistry Center, Russian Academy of Sciences, Novatorov str. 7a, Moscow, Moscow 117421, Russian Federation

Abstract

New bis(18-crown-6) and bis(aza-18-crown-6) bisstyryl dyes of pyridine series 1a,b and 2a,b containing a xylyl spacer were synthesized and their spectral and binding properties with ammonium compounds were studied by spectroscopic methods.
Homoditopic receptors 1a,b have strong absorption at 410 nm and form stable pseudocyclic 1 : 1 complexes (lgK≥5.5) with NH3+(CH2)nNH3+ (n = 2-10, 12) resulting in hypsochromic shift of their absorbance by upto 27 nm. Irradiation with visible light leads to stereospecific reaction of [2+2]-photocycloaddition (PCA) in the pseudocyclic complexes of 1a with formation of cyclobutan derivative 3. Contrarily, receptors 2a,bmax=490 nm) were found to form only non-cyclic 1 : 1 complexes with diammonium compounds.

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Financial support from the Russian Foundation for Basic Research, the Russian Academy of Sciences and the Ministry of Education and Science of Russia is gratefully acknowledged.

 

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Presentation: poster at 18th Conference on Physical Organic Chemistry, Posters, by Dmitry V. Kondratuk
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-05-24 20:45
Revised:   2009-06-07 00:44