Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, volume 230, pages 118041

Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment.

Pugachev Artem D ¹

Ozhogin Ilya V ¹

Lukyanova Maria B ¹

Lukyanov B. S. ^{2, 3}

Rostovtseva I. A. ¹

Dorogan Igor V. ¹

Makarova N. I. ¹

Tkachev Valery V.

Metelitsa Anatoly V. ¹

Aldoshin S. M. ⁴

Hide authors affiliations Show authors affiliations: 4 affiliations

Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., 344090 Rostov on Don, Russian Federation |

Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., 344090 Rostov-on-Don, Russian Federation |

Don State Technical University, 1 Gagarin sq., 344000 Rostov-on-Don, Russian Federation. |

⁴

Institute of Problems of Chemical Physics, Russian Acadeemy of Sciences, 1 Akad. Semenova ave., 142432 Chernogolovka, Moscow Region, Russian Federation. |

Publication type: Journal Article

Publication date: 2020-04-01

Elsevier

Journal: Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Quartile SCImago

Quartile WOS

Impact factor: 4.4

ISSN: 13861425

DOI: 10.1016/j.saa.2020.118041

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Spectroscopy

Analytical Chemistry

Atomic and Molecular Physics, and Optics

Instrumentation

Abstract

Photochromic molecules which can absorb and emit light within the "biological window" (650-1450 nm) are of great interest for using in various important biomedical applications such as bio-imaging, photopharmacology, targeted drug delivery, etc. Here we present three new indoline spiropyrans 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 photogenerated merocyanine isomers absorbed in the near-IR range at 708-738 nm and emitted at 768-791 nm. It was found that compound 1a with fluorine substituent possesses the most red-shifted absorption and emission bands of merocyanine form among all the known photochromic spiropyrans with maxima at 738 and 791 nm correspondingly. TD DFT calculations have shown that the longest wavelength absorption maxima of the merocyanine forms correspond to S0-S1 transitions of the isomers with at least one trans-trans-trans-configured vinylindolium fragment which brings them closer to cyanine-like structure and causes an appearance of the absorption and emission bands in the near-IR region.

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Citations by journals

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Mendeleev Communications	Mendeleev Communications, 2, 8.33% Mendeleev Communications 2 publications, 8.33%
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Frontiers in Chemistry	Frontiers in Chemistry, 1, 4.17% Frontiers in Chemistry 1 publication, 4.17%
Journal of Materials Science	Journal of Materials Science, 1, 4.17% Journal of Materials Science 1 publication, 4.17%
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1, 4.17% Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 1 publication, 4.17%
Journal of Photochemistry and Photobiology C: Photochemistry Reviews	Journal of Photochemistry and Photobiology C: Photochemistry Reviews, 1, 4.17% Journal of Photochemistry and Photobiology C: Photochemistry Reviews 1 publication, 4.17%
Topics in Current Chemistry	Topics in Current Chemistry, 1, 4.17% Topics in Current Chemistry 1 publication, 4.17%
Membranes	Membranes, 1, 4.17% Membranes 1 publication, 4.17%
ACS Applied Bio Materials	ACS Applied Bio Materials, 1, 4.17% ACS Applied Bio Materials 1 publication, 4.17%
Physical Sciences Reviews	Physical Sciences Reviews, 1, 4.17% Physical Sciences Reviews 1 publication, 4.17%
Photochemical and Photobiological Sciences	Photochemical and Photobiological Sciences, 1, 4.17% Photochemical and Photobiological Sciences 1 publication, 4.17%
ChemistrySelect	ChemistrySelect, 1, 4.17% ChemistrySelect 1 publication, 4.17%
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Citations by publishers

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Elsevier	Elsevier, 6, 25% Elsevier 6 publications, 25%
Springer Nature	Springer Nature, 6, 25% Springer Nature 6 publications, 25%
Wiley	Wiley, 4, 16.67% Wiley 4 publications, 16.67%
Pleiades Publishing	Pleiades Publishing, 2, 8.33% Pleiades Publishing 2 publications, 8.33%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 1, 4.17% Royal Society of Chemistry (RSC) 1 publication, 4.17%
Frontiers Media S.A.	Frontiers Media S.A., 1, 4.17% Frontiers Media S.A. 1 publication, 4.17%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 4.17% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 4.17%
American Chemical Society (ACS)	American Chemical Society (ACS), 1, 4.17% American Chemical Society (ACS) 1 publication, 4.17%
Walter de Gruyter	Walter de Gruyter, 1, 4.17% Walter de Gruyter 1 publication, 4.17%
	1 2 3 4 5 6

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Pugachev A. D. et al. Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment. // Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2020. Vol. 230. p. 118041.

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Pugachev A. D., Ozhogin I. V., Lukyanova M. B., Lukyanov B. S., Rostovtseva I. A., Dorogan I. V., Makarova N. I., Tkachev V. V., Metelitsa A. V., Aldoshin S. M. Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment. // Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. 2020. Vol. 230. p. 118041.

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TY - JOUR

DO - 10.1016/j.saa.2020.118041

UR - https://doi.org/10.1016%2Fj.saa.2020.118041

TI - Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment.

T2 - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

AU - Pugachev, Artem D

AU - Ozhogin, Ilya V

AU - Lukyanova, Maria B

AU - Lukyanov, B. S.

AU - Rostovtseva, I. A.

AU - Dorogan, Igor V.

AU - Makarova, N. I.

AU - Tkachev, Valery V.

AU - Metelitsa, Anatoly V.

AU - Aldoshin, S. M.

PY - 2020

DA - 2020/04/01 00:00:00

PB - Elsevier

SP - 118041

VL - 230

SN - 1386-1425

ER -

BibTex

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BibTex Copy

@article{2020_Pugachev,

author = {Artem D Pugachev and Ilya V Ozhogin and Maria B Lukyanova and B. S. Lukyanov and I. A. Rostovtseva and Igor V. Dorogan and N. I. Makarova and Valery V. Tkachev and Anatoly V. Metelitsa and S. M. Aldoshin},

title = {Visible to near-IR molecular switches based on photochromic indoline spiropyrans with a conjugated cationic fragment.},

journal = {Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy},

year = {2020},

volume = {230},

publisher = {Elsevier},

month = {apr},

url = {https://doi.org/10.1016%2Fj.saa.2020.118041},

pages = {118041},

doi = {10.1016/j.saa.2020.118041}

}

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Publisher

Elsevier

Journal

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Quartile SCImago

Quartile WOS

Impact factor

4.4

ISSN

13861425 (Print)

Labs

Laboratory of Photoactive compounds of the Research Institute of FOH SFU

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