Effects of Hydrogen Bonds on Two-Photon Absorption of Green Fluorescent Protein Chromophore Analogue

School of Physics and Electronics, Shandong Normal University, Jinan 250358, China

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Corresponding author: E-mail: zhaoke@sdnu.edu.cn

摘要

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Abstract: Effects of hydrogen bonds on two-photon absorption (TPA) of a new donor-acceptor type green fluorescent protein chromophore analogue are investigated by employing a combined molecular dynamics and quantum chemistry method. The probable configurations of the chromophore in water are extracted from molecular dynamics simulation and the TPA properties of more than twenty hydrogen bond complexes are computed by quadratic response theory. Thereby, the structure and property relations are established. Three types of hydrogen bonds including O···H−O, N−H···O and N···H−O can be formed between the chromophore and water molecules. The O···H−O induces a little decrease of TPA cross section with a red-shifted wavelength. The N−H···O gives rise to a great enhancement of TPA at a longer wavelength, while the N···H−O decreases TPA significantly and makes the wavelength blue-shifted. The reasons for these effects are rationalized well by using a two-state model analysis. The related molecular orbitals are also plotted to visualize the charge transfer characters. In addition, the averaged TPA spectrum is obtained by calculating the probabilities of various hydrogen bond complexes. Our research could provide a good insight into the design of two-photon materials by making use of hydrogen bond networks.
- Two-photon absorption /
- Hydrogen bond /
- Molecular dynamics simulation /
- Green fluorescent protein

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Figure 1. Chemical structure of two-photon chalcone (TPC) and the configuration of 30 TPC in water.

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Figure 2. Optimized geometries of TPC and various HB complexes.

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Figure 3. Frontier orbital energy levels of (A) TPC, 1, 3, 6−8, 15, and 16, and (B) 9, 12, 14, 18−20, 22, and 23.

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Figure 4. (A) TPA spectra of TPC and various HB complexes in water. The average spectrum is calculated using the population of various HB complexes. (B) TPA spectra of the HB complexes with N−H···O (solid line) and N···H−O (dash lines).

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Figure 5. Molecular orbitals in strong TPA excitations of TPC and HB complexes 1, 6, 7.

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Table I. OPA wavelength λ _op and oscillator strength f _op of the molecules in water solvent.

Molecule	λ_op/nm	f_op	Complex	λ_op/nm	f_op
TPC	377	0.76	12	369	0.91
1	385	0.82	13	368	0.92
2	384	0.82	14	377	0.86
3	391	0.88	15	396	0.93
4	390	0.88	16	398	0.71
5	388	0.72	17	376	0.78
6	388	0.73	18	400	0.87
7	361	0.81	19	377	0.95
8	368	0.81	20	404	0.78
9	396	0.80	21	375	0.89
10	394	0.78	22	384	0.93
11	394	0.80	23	406	0.85

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Table II. TPA wavelengths λ_tp and cross sections σ of the lowest absorption state of TPC and the HB complexes. The λ₀ and σ₀ are the TPA wavelength and the cross section obtained for TPC.

Molecule	λ_tp/nm	λ_tp/λ₀	σ/GM	σ/σ₀	Complex	λ_tp/nm	λ_tp/λ₀	σ/GM	σ/σ₀
TPC	770	1	133	1	12	756	0.98	60	0.45
1	790	1.03	111	0.83	13	756	0.98	53	0.40
2	788	1.02	103	0.77	14	770	1.00	82	0.62
3	816	1.06	105	0.79	15	824	1.07	74	0.56
4	814	1.06	116	0.87	16	816	1.06	197	1.48
5	793	1.03	163	1.23	17	763	0.99	122	0.92
6	793	1.03	161	1.21	18	830	1.08	117	0.88
7	732	0.95	44	0.33	19	775	1.01	40	0.30
8	749	0.97	97	0.73	20	836	1.09	172	1.29
9	819	1.06	160	1.20	21	766	0.99	67	0.50
10	816	1.06	153	1.15	22	788	1.02	61	0.46
11	814	1.06	151	1.14	23	844	1.10	129	0.97

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Table III. Two-state model analysis parameters of TPC and some HB complexes.

Complex	μ₀_f/a.u.	∆μ/a.u.	θ/(°)	ω/a.u.	δ_2SM/(10³a.u.)
TPC	3.068	5.707	169.25	0.121	65.64
1	3.225	5.296	167.60	0.118	64.54
3	3.363	4.778	164.96	0.117	58.06
6	3.062	6.263	172.78	0.118	84.31
7	3.179	3.156	82.33	0.126	6.96
9	3.238	5.854	171.73	0.115	85.51
12	3.320	3.573	152.17	0.123	25.25
16	3.046	6.591	175.63	0.115	97.88

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参考文献(31)

[1]	W. Denk, J. H. Strickler, and W. W. Webb, Science 248, 73 (1990). doi: 10.1126/science.2321027
[2]	S. Yao and K. D. Belfield, Eur. J. Org. Chem. 2012, 3199 (2012). doi: 10.1002/ejoc.201200281
[3]	D. Kim, H. G. Ryu, and K. H. Ahn, Org. Biomol. Chem. 12, 4550 (2014). doi: 10.1039/C4OB00431K
[4]	H. M. Kim and B. R. Cho, Chem. Rev. 115, 5014 (2015). doi: 10.1021/cr5004425
[5]	M. Pawlicki, H. A. Collins, R. G. Denning, and H. L. Anderson, Angew. Chem. Int. Ed. 48, 3244 (2009). doi: 10.1002/anie.200805257
[6]	H. M. Kim and B. R. Cho, Chem. Commun. 153 (2009). doi: 10.1039/b813280a
[7]	J. Wu, W. Liu, J. Ge, H. Zhang, and P. Wang, Chem. Soc. Rev. 40, 3483 (2011). doi: 10.1039/c0cs00224k
[8]	R. T. K. Kwok, C. W. T. Leung, J. W. Y. Lam, and B. Z. Tang, Chem. Soc. Rev. 44, 4228 (2015). doi: 10.1039/C4CS00325J
[9]	X. Mu, H. Zong, L. Zhu, and M. Sun, J. Phys. Chem. C 124, 2319 (2020). doi: 10.1021/acs.jpcc.9b10086
[10]	X. L. Hao, Z. J. Guo, C. Zhang, and A. M. Ren, Phys. Chem. Chem. Phys. 21, 281 (2019). doi: 10.1039/C8CP06050A
[11]	D. Wang, A. M. Ren, L. Y. Zou, J. F. Guo, and S. Huang, J. Photochem. Photobiol. A Chem. 341, 20 (2017). doi: 10.1016/j.jphotochem.2017.03.024
[12]	Y. J. Zhang, Q. Y. Zhang, H. J. Ding, X. N. Song, and C. K. Wang, Chin. Phys. B 24, 023301 (2015). doi: 10.1088/1674-1056/24/2/023301
[13]	Y. Zhang and W. Hu, Sensors 18, 4407 (2018). doi: 10.3390/s18124407
[14]	Z. Liu, P. Shao, Z. Huang, B. Liu, T. Chen, and J. Qin, Chem. Commun. 2260 (2008). doi: 10.1039/b718147g
[15]	S. Pascal, S. Denis-Quanquin, F. Appaix, A. Duperray, A. Grichine, B. Le Guennic, D. Jacquemin, J. Cuny, S. H. Chi, J. W. Perry, B. van der Sanden, C. Monnereau, C. Andraud, and O. Maury, Chem. Sci. 8, 381 (2017). doi: 10.1039/C6SC02488B
[16]	M. Y. Zhang, J. Y. Wang, C. S. Lin, and W. D. Cheng, J. Phys. Chem. B 115, 10750 (2011). doi: 10.1021/jp203977m
[17]	Y. Zhou, X. Wang, C. Tan, and C. Wang, J. Phys. Chem. A 124, 520 (2020). doi: 10.1021/acs.jpca.9b09017
[18]	S. L. Bondarev, T. F. Raichenok, S. A. Tikhomirov, N. G. Kozlov, T. V. Mikhailova, and A. I. Ivanov, J. Phys. Chem. B 125, 8117 (2021). doi: 10.1021/acs.jpcb.1c03745
[19]	K. Mendanha, R. C. Prado, L. B. A. Oliveira, and G. Colherinhas, Chem. Phys. Lett. 779, 138876 (2021). doi: 10.1016/j.cplett.2021.138876
[20]	K. Liu, Y. Wang, Y. Tu, H. Ågren, and Y. Luo. J. Phys. Chem. B 112, 4387 (2008).
[21]	Y. Şimşek and A. Brown, J. Phys. Chem. B 122, 5738 (2018). doi: 10.1021/acs.jpcb.8b00885
[22]	Y. Tu, Y. Luo, and H. Ågren, J. Phys. Chem. B 109, 16730 (2005). doi: 10.1021/jp051267t
[23]	T. B. Ren, W. Xu, Q. L. Zhang, X. X. Zhang, S. Y. Wen, H. B. Yi, L. Yuan, and X. B. Zhang, Angew. Chem. Int. Ed. 57, 7473 (2018). doi: 10.1002/anie.201800293
[24]	K. Zhao, J. Song, M. Y. Zhu, H. Zhang, and C. K. Wang, Chin. Phys. B 27, 103301 (2018). doi: 10.1088/1674-1056/27/10/103301
[25]	D. Spoel, E. Lindahl, and B. Hess, 2014 GROMACS User Manual Version 4.6.7.
[26]	J. Wang, R. M. Wolf, J. W. Caldwell, P. A. Kollman, and D. A. Case, J. Comput. Chem. 25, 1157 (2004). doi: 10.1002/jcc.20035
[27]	S. Grimme, J. Antony, S. Ehrlich, and H. Krieg, J. Chem. Phys. 132, 154104 (2010). doi: 10.1063/1.3382344
[28]	M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian 16, Revision C. 01, Wallingford CT: Gaussian Inc. (2016).
[29]	T. Lu and F. Chen, J. Comput. Chem. 33, 580 (2012). doi: 10.1002/jcc.22885
[30]	K. Aidas, C. Angeli, K. L. Bak, V. Bakken, R. Bast, L. Boman, O. Christiansen, R. Cimiraglia, S. Coriani, P. Dahle, E. K. Dalskov, U. Ekström, T. Enevoldsen, J. J. Eriksen, P. Ettenhuber, B. Fernández, L. Ferrighi, H. Fliegl, L. Frediani, K. Hald, A. Halkier, C. Hättig, H. Heiberg, T. Helgaker, A. C. Hennum, H. Hettema, E. Hjertenæs, S. Høst, I. M. Høyvik, M. F. Iozzi, B. Jansík, H. J. Aa. Jensen, D. Jonsson, P. Jørgensen, J. Kauczor, S. Kirpekar, T. Kjærgaard, W. Klopper, S. Knecht, R. Kobayashi, H. Koch, J. Kongsted, A. Krapp, K. Kristensen, A. Ligabue, O. B. Lutnæs, J. I. Melo, K. V. Mikkelsen, R. H. Myhre, C. Neiss, C. B. Nielsen, P. Norman, J. Olsen, J. M. H. Olsen, A. Osted, M. J. Packer, F. Pawlowski, T. B. Pedersen, P. F. Provasi, S. Reine, Z. Rinkevicius, T. A. Ruden, K. Ruud, V. V. Rybkin, P. Sałek, C. C. M. Samson, A. S. Merás, T. Saue, S. P. A. Sauer, B. Schimmelpfennig, K. Sneskov, A. H. Steindal, K. O. Sylvester-Hvid, P. R. Taylor, A. M. Teale, E. I. Tellgren, D. P. Tew, A. J. Thorvaldsen, L. Thøgersen, O. Vahtras, M. A. Watson, D. J. D. Wilson, M. Ziolkowski, and H. Ågren, WIREs Comput. Mol. Sci. 4, 269 (2014). doi: 10.1002/wcms.1172
[31]	N. A. Murugan, J. Kongsted, and H. Ågren, J. Chem. Theory Comput. 9, 3660 (2013). doi: 10.1021/ct400357t