Synthesis, photophysical and electrochemical properties of conjugated d-a-d systems based on 1,3,4-thiadiazoles and fused naphtho[2,1-b]thiophene derivatives

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详细

A series of 2,5-diaryl substituted 1,3,4-thiadiazoles was obtained based on fused benzothiophene-2-carboxylates and alkyl substituted 2,2’-bithiophene-5-carboxylates. The photophysical and electrochemical properties of these compounds were studied and it was determined that an increase in the conjunction chain in the donor fragment of the substituted 1,3,4-thiadiazole leads to narrowing of the band gap mainly due to an increase in the HOMO level.

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作者简介

Evgenii Uliankin

Dostoevsky Omsk State University; Omsk State Technical University

Email: fisyuk@chemomsu.ru
ORCID iD: 0000-0002-2898-5003
俄罗斯联邦, prosp. Mira, 55a, Omsk, 644077; prosp. Mira, 11, Omsk, 644050

Anastasia Kostyuchenko

Dostoevsky Omsk State University; Omsk State Technical University

Email: fisyuk@chemomsu.ru
ORCID iD: 0000-0002-4331-2560
俄罗斯联邦, prosp. Mira, 55a, Omsk, 644077; prosp. Mira, 11, Omsk, 644050

Alexander Fisyuk

Dostoevsky Omsk State University; Omsk State Technical University

编辑信件的主要联系方式.
Email: fisyuk@chemomsu.ru
ORCID iD: 0000-0001-6191-9297
俄罗斯联邦, prosp. Mira, 55a, Omsk, 644077; prosp. Mira, 11, Omsk, 644050

参考

  1. Kostyuchenko A.S., Wiosna-Salyga G., Kurow-ska A., Zagorska M., Luszczynska B., Grykien R., Glowacki I., Fisyuk A.S., Domagala W., Pron A. J. Mater. Sci. 2016, 51 (5), 2274–2282. doi: 10.1007/s10853-015-9529-4
  2. Kotwica K., Bujak P., Data P., Krzywiec W., Wamil D., Gunka P.A., Skorka L., Jaroch T., Nowakowski R., Pron A., Monkman A. Chem. Eur. J. 2016, 22 (23), 7978–7986. doi: 10.1002/chem.201600513
  3. Fukuta S., Wang Z., Miyane S., Koganezawa T., Sano T., Kido J., Mori H., Ueda M., Higashihara T. Polym. J. 2015, 47 (7), 513–521. doi: 10.1038/pj.2015.19
  4. Chen H., Liu Z., Zhao Z., Zheng L., Tan S., Yin Z., Zhu C., Liu Y. ACS Appl. Mater. Interfaces 2016, 8 (48), 33051–33059. doi: 10.1021/acsami.6b12540
  5. Kang B., Lee Y.S., Hwa J., Dongbo Z., Cho K., Kim Y.-H. Polym. Chem. 2021, 12 (12), 1758–1767. doi: 10.1039/D0PY01710H
  6. Kostyuchenko A.S., Uliankin E.B., Stasyuk A.J., Samsonenko A.L., Zheleznova T.Yu., Shatsaus-kas A.L., Fisyuk A.S.J. Org. Chem. 2022, 87 (10), 6657–6667. doi: 10.1021/acs.joc.2c00310
  7. Kurowska A., Kostyuchenko A.S., Zassowski P., Skorka L., Yurpalov V.L., Fisyuk A.S., Pron A., Domagala W.J. Phys. Chem. C. 2014, 118 (43), 25176–25189. doi: 10.1021/jp507838c
  8. Kostyuchenko A.S., Zheleznova T.Yu., Stasyuk A.J., Kurowska A., Domagala W., Pron A., Fisyuk A.S. Beilstein J. Org. Chem. 2017, 13, 313–322. doi: 10.3762/bjoc.13.34
  9. Bujak P., Kulszewicz-Bajer I., Zagorska M., Maurel V., Wielgus I., Pron A. Chem. Soc. Rev. 2013, 42 (23), 8895. doi: 10.1039/c3cs60257e
  10. Zhao Y., Guo Y., Liu Y. Adv. Mater. 2013, 25 (38), 5372–5391. doi: 10.1002/adma.201302315
  11. Hacıefendioǧlu T., Yildirim E. ACS Omega. 2022, 7 (43), 38969–38978. doi: 10.1021/acsomega.2c04713
  12. Fukuta S., Seo J., Lee H., Kim H., Kim Y., Ree M., Higashihara T. Macromolecules. 2017, 50 (3), 891–899. doi: 10.1021/acs.macromol.6b02475
  13. Kleinhenz N., Yang L., Zhou H., Price S.C., You W. Macromolecules. 2011, 44 (4), 872–877. doi: 10.1021/ma1024126
  14. Löbert M., Mishra A., Uhrich C., Pfeiffer M., Bäuerle P.J. Mater. Chem. C. 2014, 2 (24), 4879–4892. doi: 10.1039/C4TC00335G
  15. Benatto L., Koehler M.J. Phys. Chem. C. 2019, 123 (11), 6395–6406. doi: 10.1021/acs.jpcc.8b12261
  16. Kim Y.J., Cheon Y.R., Jang J.-W., Kim Y.-H., Park C.E.J. Mater. Chem. C. 2015, 3 (9), 1904–1912. doi: 10.1039/C4TC02597K
  17. Marchanka A., Maier S.K., Höger S., van Gastel M.J. Phys. Chem. B. 2011, 115 (46), 13526–13533. doi: 10.1021/jp208334y
  18. Sen A., Groß A. ACS Appl. Energy Mater. 2019, 2 (9), 6341–6347. doi: 10.1021/acsaem.9b00973
  19. Wang X., Guo L., Xia P.F., Zheng F., Wong M.S., Zhu Z. J. Mater. Chem. A. 2013, 1 (42), 13328–13336. doi: 10.1039/C3TA12901B
  20. Anthony J.E. Chem. Rev. 2006, 106 (12), 5028–5048. doi: 10.1021/cr050966z
  21. Murphy A.R., Fréchet J.M. J. Chem. Rev. 2007, 107 (4), 1066–1096. doi: 10.1021/cr0501386
  22. Rademacher P., Heinemann C., Jänsch S., Kowski K., Weiß M.E. Spectrochim. Acta Part A: Mol. Biomol. Spectroscopy. 2000, 56 (6), 1179–1190. doi: 10.1016/S1386-1425(99)00220-6
  23. Seixas de Melo J., Pina J., Rodrigues L.M., Becker R.S.J. Photochem. Photobiol. A: Chem. 2008, 194 (1), 67–75. doi: 10.1016/j.jphotochem.2007.07.014
  24. Goon I.Y., Lai L.M.H., Lim M., Munroe P., Gooding J.J., Amal R. Chem. Mater. 2009, 21 (4), 673–681. doi: 10.1021/cm8025329
  25. Liu H.-H., Chang S.-L., Huang K.-H., Cao F.-Y., Cheng K.-Y., Sun H.-S., Lai Y.-Y., Cheng Y.-J. Macromolecules. 2020, 53 (18), 7740–7748. doi: 10.1021/acs.macromol.0c01297
  26. Kostyuchenko A.S., Yurpalov V.L., Kurowska A., Domagala W., Pron A., Fisyuk A.S. Beilstein J. Org. Chem. 2014, 10, 1596–1602. doi: 10.3762/bjoc.10.165
  27. Костюченко А.С., Ульянкин Е.Б., Железнова Т.Ю., Черненко С.А., Шацаускас А.Л., Абайдулина Д.Р., Быструшкин М.О., Самсоненко А.Л., Фисюк А.С. ХГС. 2019, 55, 1262-1268. [Kostyuchenko A.S., Ulyankin E.B., Zheleznova T.Yu., Chernenko S.A., Shatsauskas A.L., Abaidulina D.R., Bystrushkin M.O., Samsonenko A.L., Fisyuk A.S. Chem. Heterocycl. Compd. 2019, 55, 1262–1268.] doi: 10.1007/s10593-019-02610-6
  28. Fisyuk A.S., Demadrille R., Querner C., Zagorska M., Bleuse J., Pron A. New J. Chem. 2005, 29 (5), 707. doi: 10.1039/b415587d
  29. Kostyuchenko A.S., Kurowska A., Zassowski P., Zheleznova T.Yu., Ulyankin E.B., Domagala W., Pron A., Fisyuk A.S.J. Org. Chem. 2019, 84 (16), 10040–10049. doi: 10.1021/acs.joc.9b01216
  30. Zapala J., Knor M., Jaroch T., Maranda-Niedbala A., Kurach E., Kotwica K., Nowakowski R., Djurado D., Pecaut J., Zagorska M., Pron A. Langmuir 2013, 29 (47), 14503–14511. doi: 10.1021/la4034707
  31. Kotwica K., Kurach E., Louarn G., Kostyuchenko A.S., Fisyuk A.S., Zagorska M., Pron A. Electrochim. Acta. 2013, 111, 491–498. doi: 10.1016/j.electacta.2013.07.209
  32. Grykien R., Luszczynska B., Glowacki I., Kurach E., Rybakiewicz R., Kotwica K., Zagorska M., Pron A., Tassini P., Maglione M.G., Mauro A.D.G.D., Fasolino T., Rega R., Pandolfi G., Minarini C., Aprano S. Optical Mater. 2014, 37, 193–199. doi: 10.1016/j.optmat.2014.05.023
  33. Kotwica K., Kostyuchenko A.S., Data P., Marszalek T., Skorka L., Jaroch T., Kacka S., Zagorska M., Nowakowski R., Monkman A.P., Fisyuk A.S., Pisula W., Pron A. Chem. Eur. J. 2016, 22 (33), 11795–11806. doi: 10.1002/chem.201600984
  34. Ulyankin E.B., Kostyuchenko A.S., Chernenko S.A., Bystrushkin M.O., Samsonenko A.L., Shatsaus-kas A.L., Fisyuk A.S. Synthesis. 2021, 53 (14), 2422–2434. doi: 10.1055/a-1416-4924
  35. Kostyuchenko A.S., Averkov A.M., Fisyuk A.S. Org. Lett. 2014, 16 (7), 1833–1835. doi: 10.1021/ol500356w
  36. Trasatti S. Pure Appl. Chem. 1986, 58 (7), 955–966. doi: 10.1351/pac198658070955
  37. Williams A.T.R., Winfield S.A., Miller J.N. Analyst. 1983, 108 (1290), 1067. doi: 10.1039/an9830801067
  38. Brouwer A.M. Pure Appl. Chem. 2011, 83 (12), 2213–2228. doi: 10.1351/PAC-REP-10-09-31
  39. Allen M.W. Measurement of Fluorescence Quantum Yields, Thermo Fisher Scientific, technical note 52019, Madison, WI, USA, 2010.

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2. Scheme

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3. Fig. 1. Starting thiophene-2-carboxylates 1a–d.

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4. Fig. 2. Normalized absorption (a) and emission (б) spectra of dilute solutions of compounds 5a (1), 5b (2), 5c (3) and 5d (4) in THF (C = 1.6 ‧ 10–6 M).

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5. Fig. 3. Cyclic voltammograms of 10–3 M solutions of compounds 5a (1), 5b (2), 5c (3), and 5d (4), recorded in 0.1 M Bu4NPF6 solution in CH2Cl2 for the anodic potential range and in THF for the cathodic potential range. Scan rate is 100 mV/s.

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6. Fig. 4. Absolute values ​​of ionization potential (IP) and electron affinity (EA) of compounds 5a–d.

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