New spiropyrans for creating elements of molecular electronics and photonics

Pugachev, A.D.; Ozhogin, I.V.; Lukyanova, M.B.; Lukyanov, B.S.; Kozlenko, A.S.; Rostovtseva, I.A.; Makarova, N.I.; Metelitsa, A.V.; Tkachev, V.V.

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New spiropyrans for creating elements of molecular electronics and photonics

Authors

Date of publication

2020

DOI

10.31114/2078-7707-2020-3-139-146

Abstract

Photochromic molecules which can absorb and emit light within the near-IR range(NIR) (650 – 1450 nm) are of great interest for using in molecular electronics and photonics. Here we report on new indolinespiropyrans containing conjugated cationic fragments and halogen substituents in the 2H-chromene moiety which were synthesized by a simple one-pot method. The molecular structure of the obtained compounds was confirmed by FT-IR, 1H and 13C NMR spectroscopy (including 2D methods), HRMS, elemental and single crystal X-ray analysis. Photochemical studies revealed the photochromic activity of spiropyrans at room temperature which caused photoswitchable fluorescence in the near-IR region after UV-irradiation. While the spirocyclic forms of compounds demonstrated absorption bands in the UV-Vis spectra with maxima in the visible region at about 445 nm and were not fluorescent, the photogeneratedmerocyanine isomers absorbed in the near-IR range at 708-738 nm and emitted at 764-790 nm depending on substituent.

Keywords

molecularelectronic, molecularswitches, spiropyrans

Library reference

Pugachev A.D., Ozhogin I.V., Lukyanova M.B., Lukyanov B.S., Kozlenko A.S., Rostovtseva I.A., Makarova N.I., Metelitsa A.V., Tkachev V.V. New spiropyrans for creating elements of molecular electronics and photonics // Problems of Perspective Micro- and Nanoelectronic Systems Development - 2020. Issue 3. P. 139-146. doi:10.31114/2078-7707-2020-3-139-146

URL of paper

http://www.mes-conference.ru/data/year2020/pdf/D086.pdf