Acenaphto[1,2-k]fluoranthene: Role of the Carbon Framework Transformation for Tuning Electronic Properties

V. A. Brotsman; Броцман В. А.; N. S. Lukonina; Луконина Н. С.; A. V. Rybalchenko; Рыбальченко А. В.; M. P. Kosaya; Косая М. П.; I. N. Ioffe; Иоффе И. Н.; K. A. Lysenko; Лысенко К. А.; L. N. Sidorov; Сидоров Л. Н.; S. A. Pshenichnyuk; Пшеничнюк С. А.; N. L. Asfandiarov; Асфандиаров Н. Л.; A. A. Goryunkov; Горюнков А. А.

doi:10.31857/S004445372307004X

Acenaphto[1,2-k]fluoranthene: Role of the Carbon Framework Transformation for Tuning Electronic Properties

Authors: Brotsman V.A.¹, Lukonina N.S.¹, Rybalchenko A.V.¹, Kosaya M.P.¹, Ioffe I.N.¹, Lysenko K.A.¹, Sidorov L.N.¹, Pshenichnyuk S.A.², Asfandiarov N.L.², Goryunkov A.A.¹
Affiliations:
1. Faculty of Chemistry, Moscow State University
2. Goryunkov Institute of Molecular and Crystal Physics, Ufa Federal Research Center, Russian Academy of Sciences
Issue: Vol 97, No 7 (2023)
Pages: 996-1010
Section: СТРОЕНИЕ ВЕЩЕСТВА И КВАНТОВАЯ ХИМИЯ
Submitted: 27.02.2025
Published: 01.07.2023
URL: https://permmedjournal.ru/0044-4537/article/view/668707
DOI: https://doi.org/10.31857/S004445372307004X
EDN: https://elibrary.ru/SKBBZT
ID: 668707

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

Acenaphtho[1,2-k]fluoranthene (1) is synthesized via tandem cyclization during the dehydrofluorination of 1,4-di(1-naphthyl)-2,5-difluorobenzene (2) on activated γ-Al2O3. Presence of residual hydroxyl groups in alumina reduce the yield of target product 1 because of the side hydrolysis of fluoroarenes with the formation a product of partial cyclization, 9-(1-naphthyl)fluoranthen-8-ol (1b). The formation of negative ions (NI) of compounds 1 and 2 in the gas phase is studied by means of dissociative electron attachment (DEA) spectroscopy. Long-lived molecular NIs 1 and 2 are registered at the thermal energies of electrons, and patterns of their fragmentation are established. The adiabatic electron affinities of compounds 1 and 2 are estimated in the Arrhenius approximation and equal 1.17 ± 0.12 and 0.71 ± 0.07 eV, respectively, which agree with data from quantum chemical modeling at the level of the density functional theory (DFT). Electronic transitions for compounds 1 and 2 are studied via optical absorption and fluorescence spectroscopy. Fluorescence quantum yields are measured, and the resulting data are interpreted according to the time dependent DFT. The electrochemical properties of compounds 1, 1b, and 2 are studied via cyclic voltamperometry, and the levels of boundary molecular orbitals are estimated on the basis of their formal potentials of reduction and oxidation.

Keywords

polycyclic aromatic hydrocarbons, dehydrofluorination, electron affinity, dissociative electron capture, spectroscopy, negative ions, cyclic voltamperometry, absorption spectroscopy, electronic transitions, fluorescence time, dependent, density functional theory

References

Ostroverkhova O. // Chem. Rev. 2016. V. 116. № 22. P. 13279.
Wang C., Dong H., Hu W. et al. // Ibid. 2012. V. 112. № 4. P. 2208.
Segawa Y., Ito H., Itami K. // Nat. Rev. Mater. 2016. V. 1. № 1. P. 15002.
Solà M. // Front. Chem. 2013. V. 1. P. 22.
Majewski M.A., Stępień M. // Angew. Chem. Int. Ed. 2019. V. 58. № 1. P. 86.
Amsharov K.Yu., Kabdulov M.A., Jansen M. // Ibid. 2012. V. 51. № 19. P. 4594.
Koper C., Sarobe M., Jenneskens L.W. // Phys. Chem. Chem. Phys. 2004. V. 6. № 2. P. 319.
Lu R.-Q., Zheng Y.-Q., Zhou Y.-N. et al. // J. Mater. Chem. A. 2014. V. 2. № 48. P. 20515.
Akhmetov V., Feofanov M., Papaianina O. et al. // Chem. Eur. J. 2019. V. 25. № 50. P. 11609.
Gracheva S.V., Yankova T.S., Kosaya M.P. et al. // Phys. Chem. Chem. Phys. 2022. V. 24. № 4. P. 26998.
Sheldrick G.M. // Acta Cryst. 2008. V. A64. P. 112.
Trasatti S. // Pure Appl. Chem. 1988. V. 58. P. 955.
Cardona C.M., Li W., Kaifer A.E. et al. // Adv. Mater. 2011. V. 23. № 20. P. 2367.
Хвостенко В.И. Масс-спектрометрия отрицательных ионов в органической химии. М.: Наука, 1981. 163 с.
Pshenichnyuk S.A., Vorob’ev A.S., Modelli A. // J. Chem. Phys. 2011. V. 135. № 18. P. 184301.
Edelson D., Griffiths J.E., McAfee K.B. // Ibid. 1962. V. 37. № 4. P. 917.
Пшеничнюк С.А., Асфандиаров Н.Л., Воробьев А.С., Матейчик Ш. // Успехи. физ. наук. 2022. Т. 192. С. 177 (Pshenichnyuk S.A., Asfandiarov N.L., Vorob’ev A.S. et al. // Phys.-Usp. 2022. V. 65. № 2. P. 163).
Lorquet J.C. // Mass Spectrom. Rev. 1994. V. 13. № 3. P. 233.
Asfandiarov N.L., Pshenichnyuk S.A., Vorob’ev A.S. et al. // Rapid Commun. Mass Spectrom. 2015. V. 29. № 9. P. 910.
Asfandiarov N.L., Pshenichnyuk S.A., Vorob’ev A.S. et al. // Ibid. 2014. V. 28. № 14. P. 1580.
Макаров А.А., Малиновский А.Л., Рябов Е.А. // Успехи. физ. наук. 2012. Т. 182. С. 1047 (Makarov A.A., Malinovsky A.L., Ryabov E.A. // Phys.-Usp. 2012. V.55. № 10. P. 977).
Chen E.S., Chen E.C.M. // Rapid Commun Mass Spectrom. 2018. V. 32. № 7. P. 604.
Asfandiarov N.L., Muftakhov M.V., Pshenichnyuk S.A. et al. // J. Chem. Phys. 2021. V. 155. № 24. P. 244302.
Asfandiarov N.L., Muftakhov M.V., Rakhmeev R.G. et al. // J. Electron. Spectros. Relat. Phenomena. 2022. V. 256. P. 147178.
Schulz G.J. // Rev. Mod. Phys. 1973. V. 45. № 3. P. 378.
Jordan K.D., Burrow P.D. // Chem. Rev. 1987. V. 87. № 3. P. 557.
Scheer A.M., Burrow P.D. // J. Phys. Chem. B. 2006. V. 110. № 36. P. 17751.
Modelli A. // Phys. Chem. Chem. Phys. 2003. V. 5. № 14. P. 2923.
Adamo C., Barone V. // J. Chem. Phys. 1999. V. 110. № 13. P. 6158.
Weigend F., Ahlrichs R. // Phys. Chem. Chem. Phys. 2005. V. 7. P. 3297.
Granovsky A.A. Firefly v. 8.2.0 (Formerly PC GAMESS), http://classic.chem.msu.su/gran/firefly/index.html. 2016.
Schmidt M.W., Baldridge K.K., Boatz J.A. et al. // J. Comput. Chem. 1993. V. 14. № 11. P. 1347.
Vladimir A., Mikhail F., Amsharov K. // RSC Adv. 2020. V. 10. № 18. P. 10879.
Papaianina O., Amsharov K.Yu. // Chem. Commun. 2016. V. 52. № 7. P. 1505.
Amsharov K. // Phys. Status Solidi B. 2016. V. 253. № 12. P. 2473.
Bayer J., Herberger J., Holz L. et al. // Chem. Eur. J. 2020. V. 26. № 72. P. 17546.
Papaianina O., Akhmetov V.A., Goryunkov A.A. et al. // Angew. Chem. Int. Ed. 2017. V. 56. № 17. P. 4834.
Prins R. // J. Catal. 2020. V. 392. P. 336.
Levin I., Brandon D. // J. Am. Ceram. Soc. 2005. V. 81. № 8. P. 1995.
Илленбергер Е., Смирнов Б.М. // Успехи. физ. наук. 1998. Т. 168. С. 731 (Illenberger E., Smirnov B.M. // Phys.-Usp. 1998. V. 41. № 7. P. 651).
Christophorou L.G. // Adv. Electron. Electron Phys. 1978. V. 46. P. 55.
Collins P.M., Christophorou L.G., Chaney E.L. et al. // Chem. Phys. Lett. 1970. V. 4. № 10. P. 646.
Васильев Ю.В., Мазунов В.А. // Письма в ЖЭТФ. 1990. Т. 51. С. 129 (Vasil’ev Yu.V., Mazunov V.A. // JETP Lett. 1990. V. 51. P. 144).
Spisak S.N., Li J., Rogachev A.Yu. et al. // Organometallics. 2016. V. 35. P. 3105.
Plummer B.F., Steffen I.K., Braley T.L. et al. // J. Am. Chem. Soc. 1993. V. 115. P. 11542.
Berlman I. Handbook of florescence spectra of Aromatic Molecules. 2nd Edition. New York and London: Academic Press. 1971. P. 473.
Clar E., Stephen J.F. // Tetrahedron. 1964. V. 20. № 6. P. 1559.
Plummer B.F., Plummer J.M., Reese W.G. // J. Phys. Chem. 1994. V. 98. № 31. P. 7470.
Bard A.J., Faulkner L.R. Electrochemical methods: fundamentals and applications. 2nd ed. New York: Wiley, 2001. P. 833.