Synthesis and luminescence properties of (Z)-2-(difluoroboryl)-3-(quinolin-2-ylmethylidene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one, a new unsymmetrical BODIPY analogue

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Acesso é pago ou somente para assinantes

Resumo

The reaction of dibenzo[b, e][1,4]dioxin-2,3-dicarbonitrile with sodium butoxide in butanol followed by treatment with nitric acid gave 1H-benzo[5,6][1,4]dioxino[2,3-f]isoindole-1,3(2H)-dione. Its condensation with quinaldine leads to the formation of (E, Z)-3-(quinolin-2-ylmethylene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one, which was treated with BF3‧Et2O in the presence of triethylamine in toluene to obtain a new unsymmetrical analog of BODIPY, (Z)-2-(difluoroboryl)-3-(quinolin-2-ylmethylene)-2,3-dihydro-1H-benzo[5,6][1,4]dioxino[2,3-f]isoindol-1-one. The complex exhibits a Stokes shift of 36 nm and a high relative fluorescence quantum yield (0.72). To support the experimental data, the results of DFT and TDDFT calculations are presented.

Texto integral

Acesso é fechado

Sobre autores

A. Nabasov

Ivanovo State University of Chemistry and Technology

Email: nik-galanin@yandex.ru
ORCID ID: 0009-0006-2775-9289
Rússia, prosp. Sheremetevskii, 7, Ivanovo, 153000

T. Rumyantseva

Ivanovo State University of Chemistry and Technology

Email: nik-galanin@yandex.ru
ORCID ID: 0000-0002-4110-0572
Rússia, prosp. Sheremetevskii, 7, Ivanovo, 153000

N. Galanin

Ivanovo State University of Chemistry and Technology

Autor responsável pela correspondência
Email: nik-galanin@yandex.ru
ORCID ID: 0000-0001-6117-167X
Rússia, prosp. Sheremetevskii, 7, Ivanovo, 153000

V. Baklagin

Yaroslavl State Technical University

Email: nik-galanin@yandex.ru
ORCID ID: 0000-0002-0060-1653
Rússia, prosp. Moskovskii, 88, Yaroslavl, 150023

M. Abramova

Yaroslavl State Technical University

Email: nik-galanin@yandex.ru
ORCID ID: 0000-0003-1721-3646
Rússia, prosp. Moskovskii, 88, Yaroslavl, 150023

I. Abramov

Yaroslavl State Technical University

Email: nik-galanin@yandex.ru
ORCID ID: 0000-0002-8204-1660
Rússia, prosp. Moskovskii, 88, Yaroslavl, 150023

Bibliografia

  1. Treibs A., Kreuzer F.-H. Lieb. Ann. Chem. 1968, 718, 208–223. doi: 10.1002/jlac.19687180119
  2. Loudet A., Burgess, K. Chem. Rev. 2007, 107, 4891–4932. doi: 10.1021/cr078381n
  3. Schmitt A., Hinkeldey B., Wild M., Jung G. J. Fluoresc. 2009, 19, 755–759. doi: 10.1007/s10895–008–0446–7
  4. Молчанов Е.Е., Марфин Ю.С., Ксенофонтов А.А., Румянцев Е.В. Изв. высш. учебн. завед. Хим. и хим. технол. 2019, 62, 13–18. doi: 10.6060/ivkkt.20196212.6017
  5. Parhi A.K., Kung M.-P., Ploessl K., Kung H.F. Tetrahedron Lett. 2008, 49, 3395–3399. doi: 10.1016/j.tetlet.2008.03.130
  6. Liu H., Lu H., Zhou Z., Shimizu S., Li Z., Kobayashi N., Shen Z. Chem. Commun. 2015, 51, 1713–1716. doi: 10.1039/C4CC06704E
  7. Wu Y., Lu H., Wang S., Li Z., Shen Z. J. Mater. Chem. C. 2015, 3, 12281–12289. doi: 10.1039/c5tc03084f
  8. Yu C., Fang X., Wu Q., Jiao L., Sun L., Li Z., So P.-K., Wong W.-Y., Hao E. Org. Lett. 2020, 22, 4588–4592. doi: 10.1021/acs.orglett.0c00940
  9. Zhang X.F., Zhang G.Q., Zhu J. J. Fluoresc. 2019, 29, 407–416. doi: 10.1007/s10895–019–02349–5
  10. Yue J., Wang N., Wang J., Tao Y., Wang H., Liu J., Zhang J., Jiao J., Zhao W. Anal. Methods. 2021, 13, 2908–2914. doi: 10.1039/D1AY00740H
  11. Cao T., Gong D., Zheng L., Wang J., Qian J., Liu W., Cao Y., Iqbal K., Qin W., Iqbal A. Anal. Chim. Acta. 2019, 1078, 168–175. doi: 10.1016/j.aca.2019.06.033
  12. He H., Lo P.-C., Yeung S.-L., Fong W.-P., Ng D.K.P. Chem. Commun. 2011, 47, 4748–4750. doi: 10.1039/C1CC10727E
  13. Gut A., Ciejka J., Makuszewski J., Majewska I., Brela M., Lapok L. Spectrochim. Acta. A: Mol. Biomol. Spec. 2022, 271, 120898. doi: 10.1016/j.saa.2022.120898
  14. Duran-Sampedro G., Agarrabeitia A.R., Garcia-Moreno I., Gartzia-Rivero L., de la Moya S., Banuelos J., Lopez-Arbeloa I., Ortiz M.J. Chem. Commun. 2015, 51, 11382–11385. doi: 10.1039/C5CC03408F
  15. Zhou Y., Xiao Y., Li D., Fu M., Qian X. J. Org. Chem. 2008, 73, 1571–1574. doi: 10.1021/jo702265x
  16. Nabasov A.A., Koptyaev A.I., Usoltsev S.D., Rumyantseva T.A., Galanin N.E. Macroheterocycles. 2022, 15, 128–132. doi: 10.6060/mhc224262g
  17. Abramov I.G., Smirnov A.V., Abramova M.B., Plakhtinsky V.V. Chem. Heterocycl. Compd. 2000, 36, 1062–1065. doi: 10.1023/A:1002786015976
  18. Oliver S.W., Smith T.D. J. Chem. Soc. Perkin Trans. II. 1987, 1579–1582. doi: 10.1039/P29870001579
  19. Brouwer A.M. Pure Appl. Chem. 2011, 83, 2213–2228. doi: 10.1351/PAC-REP-10–09–31
  20. Suzuki K., Kobayashi A., Kaneko S., Takehira K., Yoshihara T., Ishida H., Shiina Y., Oishi S., Tobita S. Phys. Chem. Chem. Phys. 2009, 11, 9850–9860. doi: 10.1039/B912178A
  21. Becke A.D. J. Chem. Phys. 1993, 98, 5648–5652. doi: 10.1063/1.464913
  22. Slater J.C. Phys. Rev. 1951, 81, 385–390. doi: 10.1103/PhysRev.81.385
  23. Perdew J.P., Wang Y. Phys. Rev. B. 1992, 45, 13244–13249. doi: 10.1103/PhysRevB.45.13244
  24. Rappoport D., Furche F. J. Chem. Phys. 2010, 133, 134105. doi: 10.1063/1.3484283
  25. Granovsky A.A. Firefly, V. 8.2.0 http://classic.chem.msu.su/gran/gamess/index.html
  26. Andrienko G.A. Chemcraft, V.1.8. http://www.chemcraftprog.com

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2. Scheme 1

Baixar (66KB)
Metadados
3. Scheme 2

Baixar (79KB)
Metadados
4. Fig. 1. Electronic absorption (1), excitation (2) and fluorescence (λEx = 400 nm) (3) spectra of compound 1 in chloroform

Baixar (69KB)
Metadados
5. Fig. 2. Electronic absorption (1), excitation (2) and fluorescence (λEx = 440 nm) (3) spectra of compound 2 in chloroform

Baixar (73KB)
Metadados
6. Fig. 3. Forms and energies of the boundary orbitals of compounds 1 and 2 a E, orbital energy, eV; b ΔE = EHOMO – EHBMO, eV.

Baixar (611KB)
Metadados
7. Fig. 4. Electronic absorption spectrum of compound 1 in chloroform compared with the theoretical one. Here and in Fig. 5: f is the oscillator strength, H is the HOMO, L is the LUMO.

Baixar (97KB)
Metadados
8. Fig. 5. Electronic absorption spectrum of compound 2 in chloroform in comparison with theoretical

Baixar (97KB)
Metadados
9. Figure from Contents

Baixar (120KB)
Metadados

Estatísticas

Vusuaização

Resumo: 996

Dimensions

Estatísticas dos artigos

Carregando as estatísticas...

PlumX


Declaração de direitos autorais © Russian Academy of Sciences, 2024