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Influence of intramolecular hydrogen bond formation sites on fluorescence mechanism |
| Hong-Bin Zhan(战鸿彬)1, Heng-Wei Zhang(张恒炜)1, Jun-Jie Jiang(江俊杰)1, Yi Wang(王一)1,†, Xu Fei(费旭)2, and Jing Tian(田晶)1 |
1 School of Biological Engineering, Dalian Polytechnic University, Dalian 116034, China;
2 Laboratory Analyst of Network Information Center, Dalian Polytechnic University, Dalian 116034, China |
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Abstract The fluorescence mechanism of HBT-HBZ is investigated in this work. A fluorescent probe is used to detect HClO content in living cells and tap water, and its structure after oxidation by HClO (HBT-ClO) is discussed based on the density functional theory (DFT) and time-dependent density functional theory (TDDFT). At the same time, the influence of the probe conformation and the proton transfer site within the excited state molecule on the fluorescence mechanism are revealed. Combined with infrared vibrational spectra and atoms-in-molecules theory, the strength of intramolecular hydrogen bonds in HBT-HBZ and HBT-ClO and their isomers are demonstrated qualitatively. The relationship between the strength of intramolecular hydrogen bonds and dipole moments is discussed. The potential energy curves demonstrate the feasibility of intramolecular proton transfer. The weak fluorescence phenomenon of HBT-HBZ in solution is quantitatively explained by analyzing the frontier molecular orbital and hole electron caused by charge separation. Moreover, when strong cyan fluorescence occurs in solution, the corresponding molecular structure should be HBT-ClO(T). The influence of the intramolecular hydrogen bond formation site on the molecule as a whole is also investigated by electrostatic potential analysis.
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Received: 23 July 2021
Revised: 22 August 2021
Accepted manuscript online: 24 September 2021
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PACS:
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82.39.Jn
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(Charge (electron, proton) transfer in biological systems)
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31.15.ee
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(Time-dependent density functional theory)
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87.15.A-
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(Theory, modeling, and computer simulation)
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| Fund: Project supported by the Open Project of State Key Laboratory of Molecular Reaction Dynamics in Dalian Institute of Chemical Physics (DICP), Chinese Academy of Sciences. |
Corresponding Authors:
Yi Wang
E-mail: wangyi@dlpu.edu.cn
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Cite this article:
Hong-Bin Zhan(战鸿彬), Heng-Wei Zhang(张恒炜), Jun-Jie Jiang(江俊杰), Yi Wang(王一), Xu Fei(费旭), and Jing Tian(田晶) Influence of intramolecular hydrogen bond formation sites on fluorescence mechanism 2022 Chin. Phys. B 31 038201
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[1] Henrique de Araujo T, Okada S S, Ghosn E E B, Taniwaki N N, Rodrigues M R, Rogerio de Almeida S, Mortara R A, Russo M, Campa A and Albuquerque R C 2013 Cell. Immunol. 281 27
[2] Sugiyama S, Okada Y, Sukhova G K, Virmani R, Heinecke J W and Libby P 2001 Am. J. Pathol. 158 879
[3] Steinbeck M J, Nesti L J, Sharkey P F and Parvizi J 2007 J. Orthop. Res. 25 1128
[4] Güngör N, Knaapen A M, Munnia A, Peluso M, Haenen G R, Chiu R K, Godschalk R W L and van Schooten F J 2010 Mutagenesis 25 149
[5] Yap Y W, Whiteman M and Cheung N S 2007 Cell Signal. 19 219
[6] Duan C, Won M, V erwilst P, Xu J C, Kim H S, Zeng L T and Kim J S 2019 Anal. Chem. 91 4172
[7] Zhu L M, Xu J C, Sun Z, Fu B Q, Qin C Q, Zeng L T and Hu X C 2015 Chem. Commun. 51 1154
[8] Huang Y F, Zhang Y B, Huo F J, Liu Y M and Yin C X 2020 Dyes Pigm. 179 108387
[9] Yuan L, Wang L, Agrawalla B K, Park S J, Zhu H, B Sivaraman, Peng J, Xu Q H and Chang Y T 2015 J. Am. Chem. Soc. 137 5930
[10] Wu L, Wu I C, DuFort C C, Carlson M A, Wu X, Chen L, Kuo C T, Qin Y, Yu J, Hingorani S R and Chiu D T 2017 J. Am. Chem. Soc. 139 6911
[11] Li Y A, Yang S, Li Q Y, Ma J P, Zhang S and Dong Y B 2017 Inorg. Chem. 56 13241
[12] Song X, Dong B, X Kong, Wang C, Zhang N and Lin W 2018 Spectrochim. Acta Part A 188 394
[13] Wen H, Huang Q, Yang X F and Li H 2013 Chem. Commun. 49 4956
[14] Majumdar P and Zhao J 2015 J. Phys. Chem. B 119 2384
[15] Wang J, Liu X and Pang Y 2014 J. Mater. Chem. B 2 6634
[16] Xu P F, Liu M H, Gao T, Zhang H L, Li Z W, Huang X Y and Zeng W B 2015 Tetrahedron. Lett. 56 4007
[17] Goswami S, Manna A, Paul S, Das A K, Nandi P K, Maity A K and Saha P 2014 Tetrahedron Lett. 55 490
[18] Chang C C, Wang F, Qiang J, Zhang Z J, Chen Y H, Zhang W, Wang Y and Chen X Q 2017 Sens. Actuators B Chem. 243 22
[19] Yang Y, Qiu F Z, Wang Y Z, Feng Y, Song X R, Tang X L, Zhang G L and W S 2018 Sens. Actuators B Chem. 260 832
[20] Wang J Y, Qu J B, Zhang H T, Wei K and Ni S X 2019 RSC Adv. 9 16467
[21] Nguyen K H, Hao Y, Zeng K, Fan S N, Li F, Yuan S, Ding X J, Xu M T and Liu Y N 2018 Spectrochim. Acta Part A 199 189
[22] He Y H, Xu Y, Shang Y T, Zheng S W, Chen W H and Pang Y 2018 Anal. Bioanal. Chem. 410 7007
[23] Tang L J, Zhou L, Yan X M, Zhong K L, Gao X, Liu X Y and Li J R 2020 Dyes Pigm. 182 108644
[24] Zhao J Z, Ji S M, Chen Y H, Guo H M and Yang, P 2012 Phys. Chem. Chem. Phys. 14 8803
[25] Zhou P W, Hoffmann M R, Han K L and He G Z 2015 J. Phys. Chem. B 119 2125
[26] Hu R, Feng J, Hu D H, Wang S Q, Li S Y, Li Y and Yang G Q 2010 Angew. Chem. Int. Ed. 49 4915
[27] Liu B, Wang H, Wang T S, Bao Y Y, Du F F, Tian J, Li Q B and Bai R K 2012 Chem. Commun. 48 2867
[28] Murale D P, Kim H, Choi W S and Churchill D G 2013 Org. Lett. 15 3946
[29] Xu Z, Xu L, Zhou J, Xu Y F, Zhu W P and Qian X H 2012 Chem. Commun. 48 10871
[30] Zhou P W and Han K L 2018 Acc. Chem. Res. 51 1681
[31] Tang Z, Yang Y F, Yang Y, Wang Y, Tian J and Fei X 2018 J. Lumin. 194 785
[32] Tang Z, Lu, M H, Liu K J, Zhao, Y L, Qi Y T, Wang Y, Zhang P and Zhou P W 2018 J. Photoch. Photobio. A 367 261
[33] Tang Z, Wei H W and Zhou P W 2020 J. Mol. Liq. 301 112415
[34] Zhan H B, Tang Z, Li Z X, Chen X Y, Tian J, Fei X and Wang Y 2021 Spectrochim. Acta Part A 260 119993
[35] Zhao J F and Jin B 2021 J. Mol. Liq. 326 115309
[36] Tao Y P, Han L G, Han Y X and Liu Z J 2016 J. Mol. Struct. 1121 188
[37] Hanaoka K, Kikuchi K, Kojima H, Urano Y and Nagano T 2004 J. Am. Chem. Soc. 126 12470
[38] Wang K J, Xi D Z, Liu C T, Chen Y H, Gu H, Jiang L, Chen X Q and Wang F 2020 Chin. Chem. Lett. 31 2955
[39] Yang X L, He L W, Xu K X, Yang Y Z and Lin W Y 2018 New. J. Chem. 42 12361
[40] Chen W, Yang M, Luo N, Wang F, Yu R Q and Jiang J H 2019 Analyst 144 6922
[41] Li N N, Bi C F, Zhang X, Xu C G, Fan C B, Gao W S, Zong Z A, Zuo S S, Niu C F and Fan Y H 2020 J. Photoch. Photobio. A 390 112299
[42] Wang, C Y, Xu J H, Ma Q J, Bai Y, Tian M J, Sun J G and Zhang Z J 2020 Spectrochim. Acta Part A 227 117579
[43] Frisch M J, Trucks G W, Schlegel H B, et al. 2016 Gaussian 16 Revision C.01 (Gaussian, Inc., Wallingford)
[44] Yanai T, Tew D P and Handy N C 2004 Chem. Phys. Lett. 393 51
[45] Schafer A, Horn H and Ahlrichs R 1992 J. Chem. Phys. 97 2571
[46] Cances E, Mennucci B and Tomasi J 1997 J. Chem. Phys. 107 3032
[47] Cammi R and Tomasi J 1995 J. Comput. Chem. 16 1449
[48] Miertuš S, Scrocco E and Tomasi J 1981 Chem. Phys. 55 117
[49] Grimmea S, Antony J, Ehrlich S and Krieg H 2010 J. Chem. Phys. 132 154104
[50] Lu T and Chen F W 2012 J. Comput. Chem. 33 580
[51] Liu Z Y, Lu T and Chen Q X 2020 Carbon 165 461
[52] Lu T, TST calculator, http://sobereva.com/310 (accessed 8 17, 2021)
[53] Fernández-Ramos A, Ellingson B A, Meana-Pañeda R, Marques J M C and Truhlar D G 2007 Theor. Chem. Account. 118 813
[54] Emamian S, Lu T, Kruse H and Emamian H 2019 J. Comput. Chem. 40 2868
[55] Tang W, Sanville E and Henkelman G 2009 J. Phys.:Condens. Matter 21 084204
[56] Yang Y F, Luo X, Ma F C and Li Y Q 2021 Spectrochim. Acta Part A 250 119375
[57] Hunt P A, Kirchner B and Welton T 2006 Chem. Eur. J. 12 6762 |
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