Synthesis and Spectral Properties of Iodine-Substituted Dyes Based on Benzothiazolium Salts

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Two series of new thiacarbocyanines with iodine atoms in the donor and/or acceptor block have been synthesized. The absorption spectra of the iodinated dyes in the region of singlet-singlet S0-S1 and singlet-triplet S0-T1 transitions are investigated. The introduction of iodine atoms into the dye structures leads to a red shift of the absorption maximum, regardless of the position of iodine in the molecule. For dyes with two or more iodine atoms, a low-intensity long-wave absorption shoulder in the region from 650 to 1000 nm is detected, which corresponds to singlet-triplet absorption.

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作者简介

I. Malakhov

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences; Novosibirsk National Research State University

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Email: ona20083@mail.ru
俄罗斯联邦, Novosibirsk; Novosibirsk

N. Orlova

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: ona20083@mail.ru
俄罗斯联邦, Novosibirsk

V. Shelkovnikov

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences; Institute of Chemical Biology and Fundamental Medicine of the Siberian Branch of the Russian Academy of Sciences

Email: ona20083@mail.ru
俄罗斯联邦, Novosibirsk; Novosibirsk

E. Vasilyev

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

Email: ona20083@mail.ru
俄罗斯联邦, Novosibirsk

A. Chernonosov

Institute of Chemical Biology and Fundamental Medicine of the Siberian Branch of the Russian Academy of Sciences

Email: ona20083@mail.ru
俄罗斯联邦, Novosibirsk

参考

  1. Kabatc J., Jurek K. Colloid. Polym. Sci. 2014, 292, 3157–3168. doi: 10.1007/s00396-014-3343-4
  2. Choi J.K., D’Urso A., Trauernicht M., Shabbir-Hussain M., Holmes A.E., Balaz M. Int. J. Mol. Sci. 2011, 12, 8052–8062. doi: 10.3390/ijms12118052
  3. Кострюкова Л.В., Плютинская А.Д., Панкратов А.А., Короткевич Е.И., Прозоровский В.Н., Тихоно-ва Е.Г., Торховская Т.И., Терешкина Ю.А. Биомед. хим. 2019, 65, 507–512. [Kostryukova L.V., Plyutinskaya A.D., Pankratov A.A., Korotkevich E.I., Prozorovskiy, V.N., Tikhonova E.G., Torkhovskaya T.I., Teryoshkina Yu.A., Biochemistry (Moscow) Supplement. Ser. B: Biomed. Chem. 2020, 14, 174–179.] doi: 10.1134/S1990750820020080
  4. Ormond A.B., Freeman H.S. Materials. 2013, 6, 817–840. doi: 10.3390/ma6030817
  5. Ser J., Lee J.Y., Kim Y.H., Cho H. Int. J. Nanomed. 2020, 15, 5803–5811. doi: 10.2147/IJN.S254881
  6. Friães S., Lima E., Boto R.E., Ferreira D., Fernandes J.R., Ferreira L.F.V., Silva A.M., Reis L.V. Appl. Sci. 2019, 9, 5414–5433. doi: 10.3390/app9245414
  7. Martins T.D., Pacheco M.L., Boto R.E., Almeida P., Farinha J.P.S., Reis L.V. Dyes Pigments. 2017, 147, 120–129. doi: 10.1016/j.dyepig.2017.07.070
  8. Santos P.F., Reis L.V., Duarte I., Serrano J.P., Almeida P., Oliveira A.S., Ferreira L.F.V. Helv. Chim. Acta. 2005, 88, 1135–1143. doi: 10.1002/hlca.200590084
  9. Arunkumar E., Sudeep P.K., Kamat P.V., Nolla B.C., Smith B.D. New J. Chem. 2007, 31, 677–683. doi: 10.1039/B616224J
  10. Шелковников В.В., Пен Е.Ф., Ковалевский В.И., Васильев Е.В., Русских В.В., Герасимова Т.Н. Опт. и спектр. 2004, 97, 1034–1042. [Shelkovnikov V.V., Kovalevskii V.I., Vasil’ev E.V., Russkikh V.V., Gerasimova T.N., Pen E.F. Optics and Spectroscopy. 2004, 97, 970–977.] doi: 10.1134/1.1843960
  11. Salvador M.A., Reis L.V., Almeida P., Santos P.F. Tetrahedron. 2008, 64, 299–303. doi: 10.1016/j.tet.2007.11.004
  12. Racané L., Čičak H., Mihalić Z., Karminski-Zamola G., Tralić-Kulenović V. Tetrahedron. 2011, 67, 2760–2767. doi: 10.1016/j.tet.2011.02.037
  13. Nociarová J., Osuský P., Rakovský E., Georgiou D., Polyzos I., Fakis M., Hrobárik P. Org. Lett. 2021, 23, 3460–3465. doi: 10.1021/acs.orglett.1c00893
  14. Орлова Н.А., Колчина Е.Ф., Шакиров М.М., Герасимова Т.Н., Шелковников В.В. ЖОрХ. 2004, 74, 256–259. [Orlova N.A., Kolchina E.F., Shakirov M.M., Gerasimova T.N., Shelkovnikov V.V. Russ. J. Org. Chem. 2004, 40, 228–231.] doi: 10.1023/B:RUJO.0000034946.67023.70
  15. Khansole S.V., Mokle S.S., Sayyed M.A., Vibhute Y.B. J. Chin. Chem. Soc. 2008, 55, 871–874. doi: 10.1002/jccs.200800130

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2. Fig. 1. Iodine-substituted dyes 17–21 with a 5-(methylthio)thienyl donor fragment

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3. Fig. 2. EAS of dimethylaminobenzylidene-containing dyes 14–16 in chloroform (main transition)

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4. Fig. 3. EAS of 5-(methylthio)thiophenylene-containing dyes 17–21 in chloroform (main transition)

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5. Fig. 4. Spectral curves of molar extinction of 4-(dimethylamino)benzylidene-containing dyes 14–16 in acetonitrile, presented in a logarithmic ordinate scale

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6. Fig. 5. Spectral molar extinction curves of 5-(methylthio)thiophenylene-containing dyes 17–21 in acetonitrile, presented in a logarithmic ordinate scale

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7. Scheme 1

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8. Scheme 2

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9. Scheme 3

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10. Scheme 4

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11. Scheme 5

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