Abstract
A detailed account on the photophysics of 3-hydroxyflavone (3HF) in 27 organic solvents is reported. Dual fluorescence of neutral 3HF was observed in protic, polar, and weakly polar solvents, endowed with sufficiently high hydrogen bond accepting and/or donating capabilities. Ground-state solvent-induced 3HF deprotonation was reported in 14 cases. 3HF anion photophysics was investigated, and the deprotonation constant Kdep calculated. Previously reported models (based on solute-solvent intermolecular hydrogen bonds) to explain solvent effects on Excited-State Intramolecular Proton Transfer (ESIPT) and on solvent-induced deprotonation have been re-examined and improved in order to rationalize the observed photophysical behaviour in all the studied solvents. Hydrogen bond donor acidity and hydrogen bond acceptor basicity are shown to be key parameters. The results are discussed in the framework of the use of 3HF as an environment-sensitive fluorescent sensor in several research fields, and as a model system in the study of ESIPT reactions. Solvent effects on 3HF reactivity are also discussed, as the role of the surrounding media on the chemistry of flavonols is an emerging topic in natural product research.
Similar content being viewed by others
Change history
27 October 2020
A Correction to this paper has been published: https://doi.org/10.1039/d0pp90017f
References
A. S. Klymchenko, Acc. Chem. Res., 2017, 50, 366–375.
P. K. Sengupta, Reviews in Fluorescence, 2016, pp. 45–70.
A. S. Klymchenko and Y. Mely, Prog. Mol. Biol. Transl. Sci., 2013, 113, 35–58.
S. Protti and A. Mezzetti, Photochemistry, 2012, 40, 295–322.
P. K. Sengupta and M. Kasha, Chem. Phys. Lett., 1979, 68, 382–385.
D. McMorrow and M. Kasha, J. Phys. Chem., 1984, 88, 2235–2243.
R. Lehnig, D. Pentlehner, A. Vdovin, B. Dick and A. Slenczka, J. Chem. Phys., 2009, 131, 194307.
A. N. Bader, F. Ariese and C. Gooijer, J. Phys. Chem. A, 2002, 106, 2844–2849.
A. J. G. Strandjord and P. F. Barbara, J. Phys. Chem., 1985, 89, 2355–2361.
G. A. Brucker, T. C. Swinney and D. F. Kelley, J. Phys. Chem., 1991, 95, 3190–3195.
V. I. Tomin, in Hydrogen Bonding and Transfer in the Excited State ed. K.-L. Han and G.-J. Zhao, John Wiley & Sons, Ltd., Chichester, UK, 2010, vol. I & II, pp. 463–523, DOI: 10.1002/9780470669143.ch22.
B. Dereka, R. Letrun, D. Svechkarev, A. Rosspeintner and E. Vauthey, J. Phys. Chem. B, 2014, 119, 2434–2443.
S. Das and N. Chattopadhyay, ChemistrySelect, 2017, 2, 6078–6081.
S. A. Ahmed, B. Maity, S. Seth and D. Seth, J. Photochem. Photobiol., B, 2017, 168, 132–141.
S. Protti, A. Mezzetti, J.-P. Cornard, C. Lapouge and M. Fagnoni, Chem. Phys. Lett., 2008, 467, 88–93.
A. Douhal, M. Sanz, L. Tormo and J. A. Organero, ChemPhysChem, 2005, 6, 419–423.
P. K. Mandal and A. Samanta, J. Phys. Chem. A, 2003, 107, 6334–6339.
D. A. Parthenopoulos and M. Kasha, Chem. Phys. Lett., 1990, 173, 303–309.
S. Protti and A. Mezzetti, J. Mol. Liq., 2015, 205, 110–114.
S. Protti, A. Mezzetti, C. Lapouge and J.-P. Cornard, Photochem. Photobiol. Sci., 2008, 7, 109–119.
S. L. Studer, W. E. Brewer, M. L. Martinez and P.-T. Chou, J. Am. Chem. Soc., 1989, 111, 7643–7644.
Z. Szakács, M. Kállay and M. Kubinyi, RSC Adv., 2017, 7, 32185–32192.
M. Musialik, R. Kuzmicz, T. S. Pawlowski and G. Litwinienko, J. Org. Chem., 2009, 74, 2699–2709.
P. Chou, D. McMorrow, T. J. Aartsma and M. Kasha, J. Phys. Chem., 1984, 88, 4596–4599.
S. Protti, K. Raulin, O. Cristini, C. Kinowski, S. Turrell and A. Mezzetti, J. Mol. Struct., 2011, 993, 485–490.
E. Biagtan, E. Goldberg, R. Stephens, E. Valeroso and J. Harmon, Nucl. Instrum. Methods Phys. Res., Sect. B, 1996, 114, 88–90.
F. J. Aparicio, M. Alcaire, A. R. González-Elipe, A. Barranco, M. Holgado, R. Casquel, F. J. Sanz, A. Griol, D. Bernier, F. Dortu, S. Cáceres, M. Antelius, M. Lapis, H. Sohlström and F. Niklaus, Sens. Actuators, B, 2016, 228, 649–657.
F. J. Aparicio, M. Alcaire, A. Borras, J. C. Gonzalez, F. López-Arbelo, I. Blasczcyk-Lezak, A. R. González-Elipe and A. Barranco, J. Mater. Chem. C, 2014, 2, 6561–6573.
E. Karakus, M. Uçuncu and M. Emrullahoglu, Anal. Chem., 2016, 88, 1039–1043.
F. S. Santos, E. Ramasamy, V. Ramamurthy and F. S. Rodembusch, Photochem. Photobiol. Sci., 2014, 13, 992–996.
A. Capan, M. S. Bostan, E. Mozioglu, M. Akoz, A. C. Goren, M. S. Eroglu and T. Ozturk, J. Photochem. Photobiol., B, 2015, 153, 391–396.
A. Sytnik and I. Litvinyuk, Proc. Natl. Acad. Sci. U. S. A., 1996, 93, 12959–12963.
L. Tormo and A. Douhal, J. Photochem. Photobiol., A, 2005, 173, 358–364.
D. Loco, N. Gelfand, S. Jurinovich, S. Protti, A. Mezzetti and B. Mennucci, J. Phys. Chem. A, 2018, 122, 390–397.
S. Hofener, P. C. Kooijman, J. Groen, F. Ariese and L. Visscher, Phys. Chem. Chem. Phys., 2013, 15, 12572–12581.
Y. Nishimoto, J. Phys. Chem. A, 2016, 120, 771–784.
V. N. Agieienko, Y. V. Kolesnik and O. N. Kalugin, J. Chem. Phys., 2014, 140, 194501.
R. Salaeh, C. Prommin, W. Chansen, K. Kerdpol, R. Daengngern and N. Kungwan, J. Mol. Liq., 2018, 252, 428–438.
M. A. Bellucci and D. F. Coker, J. Chem. Phys., 2012, 136, 194505.
V. N. Agieienko and O. N. Kalugin, J. Phys. Chem. B, 2014, 118, 12251–12262.
S. Das, S. Ghosh and N. Chattopadhyay, Chem. Phys. Lett., 2016, 644, 284–287.
V. I. Tomin and D. U. Ushakou, J. Lumin., 2015, 166, 313–321.
V. I. Tomin and D. V. Ushakou, J. Appl. Spectrosc., 2015, 82, 193–199.
V. I. Tomin and D. V. Ushakou, J. Lumin., 2016, 178, 94–105.
W. L. Whaley, E. M. Okoso-amaa, C. L. Womack, A. Vladimirova, L. B. Rodgers, M. J. Risher and M. H. Abraham, Nat. Prod. Commun., 2012, 7, 1–14.
Y. A. Davila, M. I. Sancho, M. C. Almandoz and S. E. Blanco, J. Chem. Eng. Data, 2013, 58, 1706–1716.
V. I. Tomin, Opt. Spectrosc., 2012, 113, 41–52.
W. Feng, L. Lie, L. Xiang-Ping, Y. Ya-Xin, Z. Gui-Lan and C. Wen-Ju, Chin. Phys. B, 2008, 17, 1461–1466.
F. Wu, L. Ma, S. Zhang, Z. Wang and X. Cheng, Mod. Phys. Lett. B, 2015, 29, 1550181.
V. I. Tomin and R. Jaworski, J. Mol. Struct., 2009, 924, 461–465.
V. N. Agieienko, N. A. Ostrohko and O. N. Kalugin, J. Mol. Liq., 2017, 245, 27–34.
V. Ya. Degoda, V. G. Pivovarenko, I. M. Moroz and D. Yu. Shilov, J. Lumin., 2015, 165, 174–178.
W. L. F. Armarego and D. D. Perrin, Purification of Laboratory Chemicals, Reed Educational and Profesional Publishing, 4th edn, 1996, p. 143.
A. S. Klymchenko, V. G. Pivovarenko and A. P. Demchenko, Spectrochim. Acta, Part A, 2003, 59, 787–792.
A. D. Roshal, A. V. Grigorovich, A. O. Doroshenko, V. G. Pivovarenko and A. P. Demchenko, J. Photochem. Photobiol., B, 1999, 127, 89–100.
M. Voicescu, S. Ionescu and F. Gatea, J. Fluoresc., 2014, 24, 75–83.
V. I. Tomin, Opt. Spectrosc., 2011, 110, 550–556.
A. S. Klymchenko and A. P. Demchenko, New J. Chem., 2004, 28, 687–692.
A. S. Klymchenko, C. Kenfack, G. Duportail and Y. Mely, J. Chem. Sci., 2007, 119, 83–89.
A. I. Skilitsi, D. Agathangelou, I. Shulov, J. Conyard, S. Haacke, Y. Mély, A. Klymchenko and J. Léonard, Phys. Chem. Chem. Phys., 2018, 20, 7885–7895.
C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd edn, Wiley, 2004.
M. J. Kamlet, J. L. M. Abboud, M. H. Abraham and R. W. Taft, J. Org. Chem., 1983, 48, 2877–2887.
M. H. Abraham, Chem. Soc. Rev., 1993, 22, 73–83.
M. H. Abraham, P. L. Grellier, D. V. Prior, J. J. Morris and P. J. Taylor, J. Chem. Soc., Perkin Trans. 2, 1990, 521–529.
M. H. Abraham, in Computational Approaches in Supramolecular Chemistry, ed. G. Wipff, Kluwer Academic Press, 1994, pp. 63–78.
A. Mezzetti, S. Protti, C. Lapouge and J.-P. Cornard, Phys. Chem. Chem. Phys., 2011, 13, 6858–6864.
J. Guharay, B. Sengupta and P. K. Sengupta, Proteins, 2001, 43, 75–81.
G. Litwinienko and K. U. Ingold, Acc. Chem. Res., 2007, 40, 222–230.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Lazzaroni, S., Dondi, D., Mezzetti, A. et al. Role of solute-solvent hydrogen bonds on the ground state and the excited state proton transfer in 3-hydroxyflavone. A systematic spectrophotometry study. Photochem Photobiol Sci 17, 923–933 (2018). https://doi.org/10.1039/c8pp00053k
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c8pp00053k