Abstract
In contrast to the widely reported excited-state single proton-transfer, excited-state multiple proton transfer (ESMPT) containing two or more intra- or inter-molecular proton transfers has greatly expanded the research scope of the excited-state proton transfers. In recent decades, ESMPT-active organic molecules have attracted much attention owing to their unique photophysical properties, such as large magnitude Stokes shifts and dual emission. These photophysical properties facilitate the application of the organic molecules in organic solid-state lasers, fluorescent probes and sensors, and molecular switches. Herein, we introduce the fundamentals of the ESMPT and review the recent advances in different types of ESMPTs in organic molecules. Finally, we present our conclusions and the future development prospects of the ESMPT in organic molecules.
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Douhal A, Kim SK, Zewail AH. Nature, 1995, 378: 260–263
Shen JY, Chao WC, Liu C, Pan HA, Yang HC, Chen CL, Lan YK, Lin LJ, Wang JS, Lu JF, Chun-Wei Chou S, Tang KC, Chou PT. Nat Commun, 2013, 4: 2611
Cong P, Roberts G, Herek JL, Mohktari A, Zewail AH. J Phys Chem, 1996, 100: 7832–7848
Ignasiak MT, Houée-Levin C, Kciuk G, Marciniak B, Pedzinski T. ChemPhysChem, 2015, 16: 628–633
Ghosh D, Batuta S, Das S, Begum NA, Mandal D. J Phys Chem B, 2015, 119: 5650–5661
Wu JJ, Gao H, Lai R, Zhuo MP, Feng J, Wang XD, Wu Y, Liao LS, Jiang L. Matter, 2020, 2: 1233–1243
Wang X, Li ZZ, Li SF, Li H, Chen J, Wu Y, Fu H. Adv Opt Mater, 2017, 5: 1700027
Sedgwick AC, Wu L, Han HH, Bull SD, He XP, James TD, Sessler JL, Tang BZ, Tian H, Yoon J. Chem Soc Rev, 2018, 47: 8842–8880
Weller A. Naturwissenschaften, 1955, 42: 175–176
Catalán J. J Phys Chem B, 2015, 119: 2132–2139
Huang Q, Guo Q, Lan J, You J. Dyes Pigments, 2021, 193: 109497
Taylor CA, El-Bayoumi MA, Kasha M. Proc Natl Acad Sci USA, 1969, 63: 253–260
Chachisvilis M, Fiebig T, Douhal A, Zewail AH. J Phys Chem A, 1998, 102: 669–673
Bulska H. Chem Phys Lett, 1983, 98: 398–402
Chou PT, Wei CY, Chang CP, Chiu CH. J Am Chem Soc, 1995, 117: 7259–7260
Peng CY, Shen JY, Chen YT, Wu PJ, Hung WY, Hu WP, Chou PT. J Am Chem Soc, 2015, 137: 14349–14357
Tu TH, Chen YT, Chen YA, Wei YC, Chen YH, Chen CL, Shen JY, Chen YH, Ho SY, Cheng KY, Lee SL, Chen CH, Chou PT. Angew Chem Int Ed, 2018, 57: 5020–5024
Chang KH, Liu YH, Liu JC, Peng YC, Yang YH, Li ZB, Jheng RH, Chao CM, Liu KM, Chou PT. Chem Eur J, 2019, 25: 14972–14982
Jouvet C, Miyazaki M, Fujii M. Chem Sci, 2021, 12: 3836–3856
Wang CH, Liu ZY, Huang CH, Chen CT, Meng FY, Liao YC, Liu YH, Chang CC, Li EY, Chou PT. J Am Chem Soc, 2021, 143: 12715–12724
Chai S, Zhao GJ, Song P, Yang SQ, Liu JY, Han KL. Phys Chem Chem Phys, 2009, 11: 4385–4390
Kumpulainen T, Lang B, Rosspeintner A, Vauthey E. Chem Rev, 2017, 117: 10826–10939
Padalkar VS, Seki S. Chem Soc Rev, 2016, 45: 169–202
Agmon N. J Phys Chem A, 2005, 109: 13–35
Yan CC, Wang XD, Liao LS. ACS Photonics, 2020, 7: 1355–1366
Massue J, Jacquemin D, Ulrich G. Chem Lett, 2018, 47: 1083–1089
Demchenko AP, Tomin VI, Chou PT. Chem Rev, 2017, 117: 13353–13381
Takasugi M, Guendouz A, Chassignol M, Decout JL, Lhomme J, Thuong NT, Hélène C. Proc Natl Acad Sci USA, 1991, 88: 5602–5606
Guharay J, Sengupta PK. Biochem Biophysl Res Commun, 1996, 219: 388–392
Li P, Bu Y. J Phys Chem A, 2004, 108: 10288–10295
Yu X, Yamazaki S, Taketsugu T. J Phys Chem A, 2012, 116: 10566–10573
Pradhan R, Harshan AK, Krishnavilasam Chandrika GS, Srinivasan A, Lourderaj U. J Phys Chem A, 2016, 120: 9894–9906
Wu J, Chen X, Peng LY, Cui G, Xia SH. J Phys Chem A, 2022, 126: 4002–4012
Shen S, Liu X, Sun J, Wang M, Jiang Z, Xia G, Wang H. SpectroChim Acta Part A-Mol Biomol Spectr, 2019, 217: 93–100
Vendrell O, Gelabert R, Moreno M, Lluch JM. Chem Phys Lett, 2004, 396: 202–207
Vendrell O, Gelabert R, Moreno M, Lluch JM. J Am Chem Soc, 2006, 128: 3564–3574
Stoner-Ma D, Jaye AA, Ronayne KL, Nappa J, Meech SR, Tonge PJ. J Am Chem Soc, 2008, 130: 1227–1235
Ingham C. K, El-Bayoumi MA. J Am Chem Soc, 1974, 96: 1674–1682
Suzuki N, Kubota T, Ando N, Yamaguchi S. Chem Eur J, 2022, 28: e202103584
Kawanabe A, Furutani Y, Jung KH, Kandori H. J Am Chem Soc, 2009, 131: 16439–16444
Liu Y, He Y, Yang Y, Liu Y. Chem Phys Lett, 2021, 762: 138137
Yu XF, Yamazaki S, Taketsugu T. J Chem Theor Comput, 2011, 7: 1006–1015
Yamazaki S. Chem Phys, 2018, 515: 768–778
Sakota K, Okabe C, Nishi N, Sekiya H. J Phys Chem A, 2005, 109: 5245–5247
Takeuchi S, Tahara T. J Phys Chem A, 1998, 102: 7740–7753
Chou PT, Wu GR, Wei CY, Cheng CC, Chang CP, Hung FT. J Phys Chem B, 2000, 104: 7818–7829
Song P, Ma FC. Int Rev Phys Chem, 2013, 32: 589–609
Kohtani S, Tagami A, Nakagaki R. Chem Phys Lett, 2000, 316: 88–93
Wei CY, Yu WS, Chou PT, Hung FT, Chang CP, Lin TC. J Phys Chem B, 1998, 102: 1053–1064
Doroshenko AO, Posokhov EA, Verezubova AA, Ptyagina LM. J Phys Org Chem, 2000, 13: 253–265
Wei YC, Zhang Z, Chen YA, Wu CH, Liu ZY, Ho SY, Liu JC, Lin JA, Chou PT. Commun Chem, 2019, 2: 10
Folmer DE, Poth L, Wisniewski ES, Castleman Jr. AW. Chem Phys Lett, 1998, 287: 1–7
Chang CP, Yen FH, Chou PT, Wei CY. Jnl Chin Chem Soc, 1996, 43: 463–472
Serdiuk IE, Roshal AD. Dyes Pigments, 2017, 138: 223–244
Zhao J, Zheng Y. Sci Rep, 2017, 7: 44897
Wu JJ, Zhuo MP, Lai R, Zou SN, Yan CC, Yuan Y, Yang SY, Wei GQ, Wang XD, Liao LS. Angew Chem Int Ed, 2021, 60: 9114–9119
Yang WY, Lai RC, Wu JJ, Yu YJ, Yan CC, Sun CF, Wang XD, Liao LS. Adv Funct Mater, 2022, 32: 2204129
Demchenko AP, Tang KC, Chou PT. Chem Soc Rev, 2013, 42: 1379–1408
Tseng HW, Liu JQ, Chen YA, Chao CM, Liu KM, Chen CL, Lin TC, Hung CH, Chou YL, Lin TC, Wang TL, Chou PT. J Phys Chem Lett, 2015, 6: 1477–1486
Sreedevi KCG, Thomas AP, Aparna KH, Pradhan R, Reddy MLP, Lourderaj U, Srinivasan A. Chem Commun, 2014, 50: 8667–8669
Kwon JE, Park SY. Adv Mater, 2011, 23: 3615–3642
Singh RB, Mahanta S, Kar S, Guchhait N. Chem Phys, 2007, 331: 373–384
Tobita S, Yamamoto M, Kurahayashi N, Tsukagoshi R, Nakamura Y, Shizuka H. J Phys Chem A, 1998, 102: 5206–5214
Neuwahl FVR, Foggi P, Brown RG. Chem Phys Lett, 2000, 319: 157–163
Stock K, Schriever C, Lochbrunner S, Riedle E. Chem Phys, 2008, 349: 197–203
Chou PT, Wu GR, Wei CY, Cheng CC, Chang CP, Hung FT. J Phys Chem B, 1999, 103: 10042–10052
Zhang H, van der Meulen P, Glasbeek M. Chem Phys Lett, 1996, 253: 97–102
Plasser F, Barbatti M, Aquino AJA, Lischka H. J Phys Chem A, 2009, 113: 8490–8499
Tang KC, Chen CL, Chuang HH, Chen JL, Chen YJ, Lin YC, Shen JY, Hu WP, Chou PT. J Phys Chem Lett, 2011, 2: 3063–3068
Zhao J, Dong H, Zheng Y. J Phys Chem A, 2018, 122: 1200–1208
Yu XF, Yamazaki S, Taketsugu T. J Comput Chem, 2012, 33: 1701–1708
Li H, Shi Y, Yin H, Wang Y, Cong L, Jin M, Ding D. SpectroChim Acta Part A-Mol Biomol Spectr, 2015, 141: 211–215
Komoto Y, Sakota K, Sekiya H. Chem Phys Lett, 2005, 406: 15–19
Takeuchi S, Tahara T. Chem Phys Lett, 1997, 277: 340–346
Waluk J. Acc Chem Res, 2003, 36: 832–838
Takeuchi S, Tahara T. Proc Natl Acad Sci USA, 2007, 104: 5285–5290
Zhang H, Liu S, Zhang C, Fan J, Lin L, Wang C, Song Y. SpectroChim Acta Part A-Mol Biomol Spectr, 2019, 223: 117321
de Klerk JS, Bader AN, Zapotoczny S, Sterzel M, Pilch M, Danel A, Gooijer C, Ariese F. J Phys Chem A, 2009, 113: 5273–5279
Chou PT, Wu GR, Wei CY, Shiao MY, Liu YI. J Phys Chem A, 2000, 104: 8863–8871
Yu WS, Cheng CC, Chang CP, Wu GR, Hsu CH, Chou PT. J Phys Chem A, 2002, 106: 8006–8012
Shekhovtsov NA, Vinogradova KA, Nikolaenkova EB, Krivopalov VP, Bushuev MB. J Struct Chem, 2020, 61: 1521–1529
Hara A, Komoto Y, Sakota K, Miyoshi R, Inokuchi Y, Ohashi K, Kubo K, Yamamoto E, Mori A, Nishi N, Sekiya H. J Phys Chem A, 2004, 108: 10789–10793
Hsieh WT, Hsieh CC, Lai CH, Cheng YM, Ho ML, Wang KK, Lee GH, Chou PT. ChemPhysChem, 2008, 9: 293–299
Hu WP, Chen JL, Hsieh CC, Chou PT. Chem Phys Lett, 2010, 485: 226–230
Chou PT. Jnl Chin Chem Soc, 2001, 48: 651–682
Chang CP, Wen-Chi H, Meng-Shin K, Chou PT, Clements JH. J Phys Chem, 1994, 98: 8801–8805
Ishikawa H, Iwata K, Hamaguchi H. J Phys Chem A, 2002, 106: 2305–2312
Fu C, Qu J, Yu X, Cheng J, Li Q. J Mol Liquids, 2022, 353: 118847
Chung KY, Chen YH, Chen YT, Hsu YH, Shen JY, Chen CL, Chen YA, Chou PT. J Am Chem Soc, 2017, 139: 6396–6402
Wu JJ, Wang XD, Liao LS. ACS Photonics, 2019, 6: 2590–2599
Wei GQ, Yu Y, Zhuo MP, Wang XD, Liao LS. J Mater Chem C, 2020, 8: 11916–11921
Qiao C, Zhang C, Zhou Z, Yao J, Zhao YS. CCS Chem, 2022, 4: 250–258
Park S, Kwon OH, Kim S, Park S, Choi MG, Cha M, Park SY, Jang DJ. J Am Chem Soc, 2005, 127: 10070–10074
Shi YL, Wang XD. Adv Funct Mater, 2020, 31: 2008149
Yu Y, Tao YC, Zou SN, Li ZZ, Yan CC, Zhuo MP, Wang XD, Liao LS. Sci China Chem, 2020, 63: 1477–1482
Xu FF, Li YJ, Lv Y, Dong H, Lin X, Wang K, Yao J, Zhao YS. CCS Chem, 2020, 2: 369–375
Mutai T, Tomoda H, Ohkawa T, Yabe Y, Araki K. Angew Chem Int Ed, 2008, 47: 9522–9524
Zhang W, Sakurai T, Aotani M, Watanabe G, Yoshida H, Padalkar VS, Tsutsui Y, Sakamaki D, Ozaki M, Seki S. Adv Opt Mater, 2019, 7: 1801349
Chou PT, Liao JH, Wei CY, Yang CY, Yu WS, Chou YH. J Am Chem Soc, 2000, 122: 986–987
Acknowledgements
This work was financially supported by the National Natural Science Foundation of China (52173177, 21971185, 22105139) and China Postdoctoral Science Foundation (2020M681707). This project is also funded by the Collaborative Innovation Center of Suzhou Nano Science and Technology (CIC-Nano), and by the “111” Project of the State Administration of Foreign Experts Affairs of China.
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Yang, WY., Yan, CC., Wang, XD. et al. Recent progress on the excited-state multiple proton transfer process in organic molecules. Sci. China Chem. 65, 1843–1853 (2022). https://doi.org/10.1007/s11426-022-1375-y
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DOI: https://doi.org/10.1007/s11426-022-1375-y