Excited-state intramolecular double proton transfer mechanism associated with solvent polarity for 9,9-dimethyl-3,6-dihydroxy-2,7-bis(4,5-dihydro-4,4-dimethyl-2-oxazolyl)fluorene compound

References

• G. Gilli and P. Gilli, J. Mol. Struct. 552, 1–15 (2000). doi:https://doi.org/10.1016/S0022-2860(00)00454-3.
   Web of Science ®Google Scholar
• A. Sytnik and M. Kasha, Proc. Natl. Acad. Sci. USA. 91, 8627–8630 (1994). doi:https://doi.org/10.1073/pnas.91.18.8627.
   PubMed Web of Science ®Google Scholar
• D. Sicinska, D. Truhlar and P. Paneth, J. Am. Chem. Soc. 123, 7683–7686 (2001). doi:https://doi.org/10.1021/ja010791k.
   PubMed Web of Science ®Google Scholar
• T. Martínez, Acc. Chem. Res. 39, 119–126 (2006). doi:https://doi.org/10.1021/ar040202q.
   PubMed Web of Science ®Google Scholar
• S. Nagaoka, U. Nagashima, N. Ohta, M. Fujita and T. Takemura, J. Phys. Chem. 92, 166–171 (1988). doi:https://doi.org/10.1021/j100312a036.
   Web of Science ®Google Scholar
• S. Dennison, J. Guharay and P. Sengupta, Spectrochim. Acta. Part A. 55, 903–909 (1999). doi:https://doi.org/10.1016/S1386-1425(98)00314-X.
   Web of Science ®Google Scholar
• J. Kwon and S. Park, Adv. Mater. 23, 3615–3642 (2011). doi:https://doi.org/10.1002/adma.201102046.
   PubMed Web of Science ®Google Scholar
• A. Demchenko, J. Heldt, J. Waluk, P. Chou, P. Sengupta, L. Brizhik, J. del Valle and M. Kasha, Angew. Chem. Int. Ed. 53, 14316–14324 (2014). doi:https://doi.org/10.1002/anie.201405222.
   PubMed Web of Science ®Google Scholar
• S. Nagaoka and U. Nagashima, Chem. Phys. 136, 153–163 (1989). doi:https://doi.org/10.1016/0301-0104(89)80043-6.
   Web of Science ®Google Scholar
• A. Strandjord and P. Barbara, J. Phys. Chem. 89, 2355–2361 (1985). doi:https://doi.org/10.1021/j100257a041.
   Web of Science ®Google Scholar
• A. Sytnik, D. Gormin and M. Kasha, Proc. Natl. Acad. Sci. USA. 91, 11968–11972 (1994). doi:https://doi.org/10.1073/pnas.91.25.11968.
   PubMed Web of Science ®Google Scholar
• J. Zhao, Z. Li and B. Jin, J. Lumin. 238, 118231 (2021). doi:https://doi.org/10.1016/j.jlumin.2021.118231.
   Web of Science ®Google Scholar
• S. Nagaoka, Y. Bandoh, S. Matsuhiroya, K. Inoue, U. Nagashima and K. Ohara, J. Photochem. Photobiol. A. 409, 113122 (2021). doi:https://doi.org/10.1016/j.jphotochem.2020.113122.
   Web of Science ®Google Scholar
• Y. Wang, H. Yin, Y. Shi, M. Jin and D. Ding, New J. Chem. 38, 4458–4464 (2014). doi:https://doi.org/10.1039/C4NJ00458B.
   Web of Science ®Google Scholar
• Y. Liu and T. Chu, Chem. Phys. Lett. 505, 117–121 (2011). doi:https://doi.org/10.1016/j.cplett.2011.02.034.
   Web of Science ®Google Scholar
• S. Liu, J. Lu, Q. Lu, J. Fan, L. Lin, C. Wang and Y. Song, Front. Chem. 7, 932 (2020). doi:https://doi.org/10.3389/fchem.2019.00932.
   PubMed Web of Science ®Google Scholar
• M. Mal and D. Mandal, Spectrochim. Acta, Part A. 255, 119708 (2021). doi:https://doi.org/10.1016/j.saa.2021.119708.
   PubMed Web of Science ®Google Scholar
• J. Zhao, H. Dong and Y. Zheng, J. Phys. Chem. A. 122, 1200–1208 (2018). doi:https://doi.org/10.1021/acs.jpca.7b10492.
   PubMed Web of Science ®Google Scholar
• G. Kumar, K. Paul and V. Luxami, New J. Chem. 44, 12866–12874 (2020). doi:https://doi.org/10.1039/D0NJ01651A.
   Web of Science ®Google Scholar
• L. Song, X. Meng, J. Zhao, H. Han and D. Zheng, Spectrochim. Acta A. 264, 120296 (2022). doi:https://doi.org/10.1016/j.saa.2021.120296.
   PubMed Web of Science ®Google Scholar
• D.K. Rana, S. Dhar, A. Sarkar and S. Bhattacharya, J. Phys. Chem. A. 115, 9169–9179 (2011). doi:https://doi.org/10.1021/jp204165j.
   PubMed Web of Science ®Google Scholar
• Y. Chen, P. Wu, C. Peng, J. Shen, C. Tsai, W. Hu and P. Chou, Phys. Chem. Chem. Phys. 19, 28641–28646 (2017). doi:https://doi.org/10.1039/C7CP05002J.
   PubMed Web of Science ®Google Scholar
• C. Li, B. Hu, Y. Cao and Y. Li, Spectrochim. Acta, Part A. 258, 119854 (2021). doi:https://doi.org/10.1016/j.saa.2021.119854.
   PubMed Web of Science ®Google Scholar
• X. Meng, L. Song, H. Han, J. Zhao and D. Zheng, Spectrochim. Acta A. 265, 120383 (2022). doi:https://doi.org/10.1016/j.saa.2021.120383.
   Web of Science ®Google Scholar
• F. Yu, P. Li, B. Wang and K. Han, J. Am. Chem. Soc. 135, 7674–7680 (2013). doi:https://doi.org/10.1021/ja401360a.
   PubMed Web of Science ®Google Scholar
• D. Dahal, L. McDonald, X. Bi, C. Abeywickrama, F. Gombedza, M. Konopka, S. Paruchuri and Y. Pang, Chem. Commun. 53, 3697–3700 (2017). doi:https://doi.org/10.1039/C7CC00700K.
   PubMed Web of Science ®Google Scholar
• H. Dong, J. Zhao, H. Yang and Y. Zheng, ACS Appl. Bio Mater. 2, 3622–3629 (2019). doi:https://doi.org/10.1021/acsabm.9b00477.
   PubMedGoogle Scholar
• D. Ray, A. Kundu, A. Pramanik and N. Guchhait, J. Phys. Chem. B. 119, 2168–2179 (2015). doi:https://doi.org/10.1021/jp504037y.
   PubMed Web of Science ®Google Scholar
• D. Yang, J. Wu, M. Jia and X. Song, J. Chin. Chem. Soc. 64, 1385–1391 (2017). doi:https://doi.org/10.1002/jccs.201700253.
   Web of Science ®Google Scholar
• S. Jana, S. Dalapati and N. Guchhait, Photoch. Photobio. Sci. 12, 1636–1648 (2013). doi:https://doi.org/10.1039/c3pp50010a.
   PubMed Web of Science ®Google Scholar
• D. Jacquemin, J. Zúñiga, A. Requena and J. Céron-Carrasco, Acc. Chem. Res. 47, 2467–2474 (2014). doi:https://doi.org/10.1021/ar500148c.
   PubMed Web of Science ®Google Scholar
• J. Zhao, H. Dong, H. Yang and Y. Zheng, Org. Chem. Front. 5, 2710–2718 (2018). doi:https://doi.org/10.1039/C8QO00688A.
   Web of Science ®Google Scholar
• D. Heyes, S. Hardman, T. Hedison, R. Hoeven, G. Greetham, M. Towrie and N. Scrutton, Angew. Chem. 127, 1532–1535 (2015). doi:https://doi.org/10.1002/ange.201409881.
   Google Scholar
• O. Abou-Zied, R. Jimenez and F. Romesberg, J. Am. Chem. Soc. 123, 4613–4614 (2001). doi:https://doi.org/10.1021/ja003647s.
   PubMed Web of Science ®Google Scholar
• Y. Yang, X. Luo, F. Ma and Y. Li, Spectrochim. Acta A. 250, 119375 (2021). doi:https://doi.org/10.1016/j.saa.2020.119375.
   Web of Science ®Google Scholar
• H. Tseng, J. Liu, Y. Chen, C. Chao, K. Liu, C. Chen, T. Lin, C. Hung, Y. Chou, T. Lin, T. Wang and P. Chou, J. Phys. Chem. Lett. 6, 1477–1486 (2015). doi:https://doi.org/10.1021/acs.jpclett.5b00423.
   PubMed Web of Science ®Google Scholar
• J. Zhao, J. Chen, Y. Cui, J. Wang, L. Xia, Y. Dai, P. Song and F. Ma, Phys. Chem. Chem. Phys. 17, 1142–1150 (2015). doi:https://doi.org/10.1039/C4CP04135F.
   PubMed Web of Science ®Google Scholar
• H. Zheng, Y. Wang, P. Cao and P. Wu, Chem. Commun. 57, 3575–3578 (2021). doi:https://doi.org/10.1039/D1CC00207D.
   PubMed Web of Science ®Google Scholar
• A. Becke, Phys. Rev. 38, 276–282 (1988). doi:https://doi.org/10.1103/PhysRevA.38.3098.
   Web of Science ®Google Scholar
• E. Cancès, B. Mennucci and J. Tomasi, J. Chem. Phys. 107, 3032–3041 (1997). doi:https://doi.org/10.1063/1.474659.
   Web of Science ®Google Scholar
• C. Lee, W. Yang and R. Parr, Phys. Rev. B. 37, 785–789 (1988). doi:https://doi.org/10.1103/PhysRevB.37.785.
   PubMed Web of Science ®Google Scholar
• G. Zhao and K. Han, J. Phys. Chem. A. 111, 2469–2474 (2007). doi:https://doi.org/10.1021/jp068420j.
   PubMed Web of Science ®Google Scholar
• G. Zhao, J. Liu, L. Zhou and K. Han, J. Phys. Chem. B. 111, 8940–8945 (2007). doi:https://doi.org/10.1021/jp0734530.
   PubMed Web of Science ®Google Scholar
• J. Zhao, H. Dong and Y. Zheng, J. Lumin. 195, 228–233 (2018). doi:https://doi.org/10.1016/j.jlumin.2017.11.026.
   Web of Science ®Google Scholar
• V. Padalkar, Y. Tsutsui, T. Sakurai, D. Sakamaki, N. Tohnai, K. Kato, M. Takata, T. Akutagawa, K. Sakai and S. Seki, J. Phys. Chem. B. 121, 10407–10416 (2017). doi:https://doi.org/10.1021/acs.jpcb.7b08073.
   PubMed Web of Science ®Google Scholar
• S. Roh, Y. Kim, K. Seo, D. Lee, H. Kim, Y. Park, J. Park and J. Lee, Adv. Funct. Mater. 19, 1663–1671 (2009). doi:https://doi.org/10.1002/adfm.200801122.
   Web of Science ®Google Scholar
• A. Morales, K. Schafer-Hales, C. Yanez, M. Bondar, O. Przhonska, A. Marcus and K. Belfield, ChemPhysChem. 10, 2073–2081 (2009). doi:https://doi.org/10.1002/cphc.200900032.
   PubMed Web of Science ®Google Scholar
• B. Li, L. Zhou, H. Cheng, Q. Huang, J. Lan, L. Zhou and J. You, Chem. Sci. 9, 1213–1220 (2018). doi:https://doi.org/10.1039/C7SC04464J.
   PubMed Web of Science ®Google Scholar
• V. Enchev, N. Markova, M. Stoyanova, P. Petrov, M. Rogozherov, N. Kuchukova, I. Timtcheva, V. Monev, S. Angelova and M. Spassova, Chem. Phys. Lett. 563, 43–49 (2013). doi:https://doi.org/10.1016/j.cplett.2013.01.057.
   Web of Science ®Google Scholar
• D. Orr, A. Tolfrey, J. Percy, J. Frieman, Z. Harrison, M. Campbell-Crawford and V. Patel, Chem-Eur. J. 19, 9655–9662 (2013). doi:https://doi.org/10.1002/chem.201301011.
   PubMed Web of Science ®Google Scholar
• D. Göbel, D. Duvinage, T. Stauch and B. Nachtsheim, J. Mater. Chem. C. 8, 9213–9225 (2020). doi:https://doi.org/10.1039/D0TC00776E.
   Web of Science ®Google Scholar
• D. Göbel, M. Friedrich, E. Lork and B. Nachtsheim, Beilstein J. Org. Chem. 16, 1683–1692 (2020). doi:https://doi.org/10.3762/bjoc.16.139.
   PubMed Web of Science ®Google Scholar
• D. Göbel, N. Clamor and B. Nachtsheim, Org. Biomol. Chem. 16, 4071–4075 (2018). doi:https://doi.org/10.1039/C8OB01072B.
   PubMed Web of Science ®Google Scholar
• D. Göbel, N. Clamor, E. Lork and B. Nachtsheim, Org. Lett. 21, 5373–5377 (2019). doi:https://doi.org/10.1021/acs.orglett.9b01350.
   PubMed Web of Science ®Google Scholar
• D. Göbel, P. Rusch, D. Duvinage, N. Bigall and B. Nachtsheim, Chem. Commun. 56, 15430–15433 (2020). doi:https://doi.org/10.1039/D0CC05780K.
   PubMed Web of Science ®Google Scholar
• D. Göbel, P. Rusch, D. Duvinage, T. Stauch, N. Bigall and B. Nachtsheim, J. Org. Chem. 1, 1–25 (2021).
   Google Scholar
• R. Cammi and J. Tomasi, J. Comput. Chem. 16, 1449–1458 (1995). doi:https://doi.org/10.1002/jcc.540161202.
   Web of Science ®Google Scholar
• S. Miertus, E. Scrocco and J. Tomasi, Chem. Phys. 55, 117–129 (1981). doi:https://doi.org/10.1016/0301-0104(81)85090-2.
   Web of Science ®Google Scholar
• I. Petrushenko, N. Tikhonov and K. Petrushenko, Diam. Relat. Mater. 107, 107905 (2020). doi:https://doi.org/10.1016/j.diamond.2020.107905.
   Web of Science ®Google Scholar
• C. Lefebvre, H. Khartabil, J. Boisson, J. Contreras-García, J. Piquemal and E. Hénon, ChemPhysChem. 19, 724–735 (2018). doi:https://doi.org/10.1002/cphc.201701325.
   PubMed Web of Science ®Google Scholar
• W. Humphery, A. Dalke and K. Shulten, J. Mol. Graph. 14, 33–38 (1996). doi:https://doi.org/10.1016/0263-7855(96)00018-5.
   PubMedGoogle Scholar
• H. He, S. Zhang, X. Liu, J. Wang, X. Yao and X. Zhang, Fluid Phase Equilibr. 360, 169–179 (2013). doi:https://doi.org/10.1016/j.fluid.2013.09.007.
   Web of Science ®Google Scholar
• Z. Tang, Y. Wang, D. Bao, M. Lv, Y. Yang, J. Tian and L. Dong, J. Phys. Chem. A. 121, 8807–8814 (2017). doi:https://doi.org/10.1021/acs.jpca.7b08266.
   PubMed Web of Science ®Google Scholar
• J. Zhao, J. Chen, J. Liu and M. Hoffmann, Phys. Chem. Chem. Phys. 17, 11990–11999 (2015). doi:https://doi.org/10.1039/C4CP05651E.
   PubMed Web of Science ®Google Scholar
• X. Liu, Y. Wu, Z. Li and Y. Gao, Appl. Surf. Sci. 400, 1–5 (2017). doi:https://doi.org/10.1016/j.apsusc.2016.12.087.
   Web of Science ®Google Scholar
• D. Yang, J. Wu, H. Dong, M. Jia and X. Song, J. Phys. Org. Chem. 31, 3756 (2018). doi:https://doi.org/10.1002/poc.3756.
   Web of Science ®Google Scholar
• L. Cong, H. Yin, Y. Shi, M. Jin and D. Ding, RSC Adv. 5, 1205–1212 (2015). doi:https://doi.org/10.1039/C4RA09773D.
   Web of Science ®Google Scholar
• G. Zhao and K. Han, Acc. Chem. Res. 45, 404–413 (2012). doi:https://doi.org/10.1021/ar200135h.
   PubMed Web of Science ®Google Scholar
• R.F.W. Bader, Chem. Rev. 91, 893 (1991). doi:https://doi.org/10.1021/cr00005a013.
   Web of Science ®Google Scholar
• S. Emamian, T. Lu, H. Kruse and H. Emamian, J. Comput. Chem. 40, 2868–2881 (2019). doi:https://doi.org/10.1002/jcc.26068.
   PubMed Web of Science ®Google Scholar
• R. Musin and Y. Mariam, J. Phys. Org. Chem. 19, 425–444 (2006). doi:https://doi.org/10.1002/poc.1102.
   Web of Science ®Google Scholar
• Z. Tang, H. Wei and P. Zhou, J. Mol. Liq. 301, 112415 (2020). doi:https://doi.org/10.1016/j.molliq.2019.112415.
   Web of Science ®Google Scholar
• D. Yang, M. Jia, J. Wu and X. Song, Sci. Rep. 7, 11728 (2017). doi:https://doi.org/10.1038/s41598-017-12146-4.
   PubMed Web of Science ®Google Scholar
• J. Zhao and B. Jin, J. Lumin. 232, 117800 (2021). doi:https://doi.org/10.1016/j.jlumin.2020.117800.
   Web of Science ®Google Scholar
• J. Zhao and B. Jin, J. Mol. Liq. 326, 115309 (2021). doi:https://doi.org/10.1016/j.molliq.2021.115309.
   Web of Science ®Google Scholar
• M. Zhou, J. Zhao, Y. Cui, Q. Wang, Y. Dai, P. Song and L. Xia, J. Lumin. 161, 1–6 (2015). doi:https://doi.org/10.1016/j.jlumin.2014.12.049.
   Web of Science ®Google Scholar
• Z. Tang and P. Zhou, J. Phys. Chem. B. 124, 3400–3407 (2020). doi:https://doi.org/10.1021/acs.jpcb.0c01624.
   PubMed Web of Science ®Google Scholar
• Q. Zhang, X. Yang, D. Yang and S. Cheng, Chem. Phys. Lett. 730, 485–490 (2019). doi:https://doi.org/10.1016/j.cplett.2019.06.047.
   Web of Science ®Google Scholar
• H. Schlegel, J. Comput. Chem. 3, 214–218 (1982). doi:https://doi.org/10.1002/jcc.540030212.
   Web of Science ®Google Scholar
• C. Peng, P. Ayala, H. Schlegel and M. Frisch, J. Comput. Chem. 17, 49–56 (1996). doi:https://doi.org/10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO;2-0.
   Web of Science ®Google Scholar
• H. Schlegel, Theor. Chem. Acc. 66, 333–340 (1984). doi:https://doi.org/10.1007/BF00554788.
   Google Scholar