Theoretical insights into photochemical ESITP process for novel DMP-HBT-py compound

doi:10.1088/1674-1056/aba9bb

Abstract

We execute the density functional theory (DFT) and time-dependent density functional theory (TDDFT) approaches to make a detailed exploration about excited state luminescent properties as well as excited state intramolecular proton transfer (ESIPT) mechanism for the novel 2,6-dimethyl phenyl (DMP-HBT-py) system. Firstly, we check and confirm the formation and stabilization of hydrogen bonding interaction for DMP-HBT-py. Via optimized geometrical parameters of primary chemical bond and infrared (IR) spectra, we find O–H⋯N hydrogen bond of DMP-HBT-py should be strengthened in S₁ state. Insights into frontier molecular orbitals (MOs) analyses, we infer charge redistribution and charge transfer (ICT) phenomena motivate ESIPT trend. Via probing into potential energy curves (PECs) in related electronic states, we come up with the ultrafast ESIPT behavior due to low potential barrier. Furthermore, we search the reaction transition state (TS) structure, the ultrafast ESIPT behavior and mechanism of DMP-HBT-py compound can be re-confirmed. We sincerely wish this work could play roles in further developing novel applications based on DMP-HBT-py compound and in promoting efficient solid emitters in OLEDs in future.

Keywords: infrared vibrational spectra intramolecular charge transfer potential energy curve excited state intramolecular proton transfer

Received: 21 June 2020
Revised: 15 July 2020
Published: 05 October 2020

PACS:	31.15.ee	(Time-dependent density functional theory)
	31.15.ae	(Electronic structure and bonding characteristics)
	31.15.es	(Applications of density-functional theory (e.g., to electronic structure and stability; defect formation; dielectric properties, susceptibilities; viscoelastic coefficients; Rydberg transition frequencies))

Corresponding Authors: Guang Yang(杨光)

About author:

†Corresponding author. E-mail: yxd5460@163.com

* Project supported by the Science and Technology Research Project of Henan Province, China (Grant No. 172102210391) and the Higher Vocational School Program for Key Teachers from Department of Education of Henan Province, China (Grant No. 2019GZGG042).

Cite this article:

Guang Yang(杨光), Kaifeng Chen(陈凯锋), Gang Wang(王岗), Dapeng Yang(杨大鹏) Theoretical insights into photochemical ESITP process for novel DMP-HBT-py compound 2020 Chin. Phys. B 29 103103

Fig. 1.

View of DMP-HBT-py and its proton-transfer DMP-HBT-py-PT tautomer at B3LYP/TZVP (hexane solvent) level. Red: O atom; blue: H atom; yellow: C atom; violet: N atom; green: S atom.

Table 1.

Optimized geometrical parameters (bond length (in unit Å) and bond angle (in unit (°)) of hydrogen bond O–H⋯N of DMP-HBT-py and O⋯H–N of DMP-HBT-py-PT in S₀ and S₁ states based on the DFT/TDDFT methods with IEFPCM (hexane) model.

Fig. 2.

Simulated IR spectra for DMP-HBT-py (a) and DMP-HBT-py-PT (b) structures in hexane solvent in S₀ and S₁ states. (a) The O–H stretching vibrational mode of DMP-HBT-py form. (b) The H–N stretching vibrational mode of DMP-HBT-py-PT structure.

Fig. 3.

The HOMO and LUMO of DMP-HBT-py compound via TDDFT/B3LYP/TZVP theoretical level. In CDD map, the regions with increased electron densities are shown in violet, whereas those with decreased electron densities are shown in light blue.

Fig. 4.

The constructed PECs of DMP-HBT-py system via fixing O–H bond length in S₀ and S₁ states.

Table 2.

Vertical excitation energies (in unit nm), oscillator strengths (f), and relevant transition composition as well as percentage (%) for DMP-HBT-py compound.

Fig. 5.

The TS structure for DMP-HBT-py system along with ESIPT path. Herein, the imaginary frequency and its vibrational eigenvector are also shown.

[1]	Zhao G, Han K 2012 Acc. Chem. Res. 45 404 DOI: 10.1021/ar200135h
[2]	Zhao G, Han K, Lei Y, Dou Y 2007 J. Chem. Phys. 127 094307 DOI: 10.1063/1.2768347
[3]	Li J, Wu Y, Xu Z, Liao Q, Zhang H, Zhang Y, Xiao L, Yao J, Fu H 2017 J. Mater. Chem. C 5 12235 DOI: 10.1039/c7tc04207h
[4]	Zhao J, Dong H, Yang H, Zheng Y 2018 Org. Chem. Front 5 2710 DOI: 10.1039/C8QO00688A
[5]	Zhao H, Sun C, Liu X, Yin H, Shi Y 2019 Chin. Phys. B 28 018201 DOI: 10.1088/1674-1056/28/1/018201
[6]	Zhao J, Dong H, Zheng Y 2018 J. Lumin. 195 228 DOI: 10.1016/j.jlumin.2017.11.026
[7]	Miao C, Shi Y 2011 J. Comput. Chem. 32 3058 DOI: 10.1002/jcc.21888
[8]	Demchenko A, Tang K, Chou P 2013 Chem. Soc. Rev. 42 1379 DOI: 10.1039/C2CS35195A
[9]	Zhao J, Chen J, Liu J, Hoffmann M 2015 Phys. Chem. Chem. Phys. 17 11990 DOI: 10.1039/C4CP05651E
[10]	Qu R, Liu H, Feng M, Yang X, Wang Z 2012 J. Chem. Eng. Data 57 2442 DOI: 10.1021/je300407g
[11]	Li G, Chu T 2011 Phys. Chem. Chem. Phys. 13 20766 DOI: 10.1039/c1cp21470e
[12]	Liu S, Pan J, Wei D, Xu J, Zhou Y, Song Y 2019 Can. J. Phys. 97 721 DOI: 10.1139/cjp-2018-0503
[13]	Zhang M, Zhou Q, Du C, Ding Y, Song P 2016 RSC Adv. 6 59389 DOI: 10.1039/C6RA11140H
[14]	Yin H, Shi Y 2018 Chin. Phys. B 27 058201 DOI: 10.1088/1674-1056/27/5/058201
[15]	Zhao J, Dong H, Zheng Y 2018 J. Phys. Chem. A 122 1200 DOI: 10.1021/acs.jpca.7b10492
[16]	Li G, Li W, Zhang H, Sun X 2014 J. Theor. Comput. Chem. 13 1450006 DOI: 10.1142/S0219633614500060
[17]	Li G, Wang J, Zhang H, Li W, Wang F, Liang Y 2014 Chem. Phys. Lett. 616 30 DOI: 10.1016/j.cplett.2014.10.029
[18]	Ma H, Huang J 2016 RSC Adv. 6 96147 DOI: 10.1039/C6RA16907D
[19]	Zhao J, Chen J, Cui Y, Wang J, Xia L, Dai Y, Song P, Ma F 2015 Phys. Chem. Chem. Phys. 17 1142 DOI: 10.1039/C4CP04135F
[20]	Li H, Ma L, Yin H, Shi Y 2018 Chin. Phys. B 27 098201 DOI: 10.1088/1674-1056/27/9/098201
[21]	Liu S, Ma Y, Yang Y, Liu S, Li Q, Song Y 2018 Chin. Phys. B 27 023103 DOI: 10.1088/1674-1056/27/2/023103
[22]	Chen H, Zhao J, Huang J, Liang Y 2019 Phys. Chem. Chem. Phys. 21 7447 DOI: 10.1039/C9CP00374F
[23]	Zhao J, Zheng Y 2017 Sci. Rep. 7 44897 DOI: 10.1038/srep44897
[24]	Xiao H, Chen K, Cui D, Jiang N, Yin G, Wang J, Wang R 2014 New J. Chem. 38 2386 DOI: 10.1039/c3nj01557b
[25]	Stasyuk A, Chen Y, Chen C, Wu P, Chou P 2016 Phys. Chem. Chem. Phys. 18 24428 DOI: 10.1039/C6CP05236C
[26]	Tang K, Chen C, Chuang H, Chen J, Chen Y, Lin Y, Shen J, Hu W, Chou P 2011 J. Phys. Chem. Lett. 2 3063 DOI: 10.1021/jz201439w
[27]	Dahal D, McDonald L, Bi X, Abeywickrama C, Gombedza F, Konopka M, Paruchuri S, Pang Y 2017 Chem. Commun. 53 3697 DOI: 10.1039/C7CC00700K
[28]	Wang J, Li Y, Duah E, Paruchuri S, Zhou D, Pang Y 2014 J. Mater. Chem. B 2 2008 DOI: 10.1039/c3tb21339k
[29]	Zhang X, Han J, Li Y, Sun C, Su X, Shi Y, Yin H 2020 Chin. Phys. B 29 038201 DOI: 10.1088/1674-1056/ab6d50
[30]	Liu X, Yin H, Li H, Shi Y 2017 Spectrochim. Acta Part. A 177 1 DOI: 10.1016/j.saa.2017.01.022
[31]	Zhao J, Liu X, Zheng Y 2017 J. Phys. Chem. A 121 4002 DOI: 10.1021/acs.jpca.7b01404
[32]	Li H, Yin H, Liu X, Shi Y, Jin M, Ding D 2017 Spectrochim. Acta Part. A 184 270 DOI: 10.1016/j.saa.2017.05.027
[33]	Xu L, Zhang T, Zhang Q, Yang D 2020 Chin. Phys. B 29 053102 DOI: 10.1088/1674-1056/ab8208
[34]	Zhao J, Chen J, Song P, Liu J, Ma F 2015 J. Clust. Sci. 26 1463 DOI: 10.1007/s10876-014-0830-1
[35]	Wan M, Jin C, Yu Y, Huang D, shao J 2017 Chin. Phys. B 26 033101 DOI: 10.1088/1674-1056/26/3/033101
[36]	Zhao J, Yang Y 2016 J. Mol. Liq 220 735 DOI: 10.1016/j.molliq.2016.05.029
[37]	Li W, Guo B, Chang C, Guo X, Zhang M, Li Y 2016 J. Mater. Chem. A 4 10135 DOI: 10.1039/C6TA04030F
[38]	Li X, Zhai Y, Zhang M, Song Y 2018 J. Phys. Org. Chem. 31 3821
[39]	Zhao J, Song P, Ma F 2014 Commun. Comput. Chem. 2 117 DOI: 10.4208/cicc.2014.v2.n3.3
[40]	Peng C, Shen J, Chen Y, Wu P, Hung W, Hu W, Chou P 2015 J. Am. Chem. Soc. 137 14349 DOI: 10.1021/jacs.5b08562
[41]	Abeywickrama C, Wijesinghe K, Stahelin R, Pang Y 2017 Chem. Commun. 53 5886 DOI: 10.1039/C7CC03417B
[42]	Zhao J, Dong H, Yang H, Zheng Y 2019 ACS Appl. Bio. Mater. 2 5182 DOI: 10.1021/acsabm.9b00818
[43]	Kumar G, Paul K, Luxami V 2020 New J. Chem. 44 12866 DOI: 10.1039/d0nj01651a
[44]	Nguyen H, Trinh B, Nguyen N, Dang S, Phama H, Dguyen L 2011 Phytochem. Lett. 4 48 DOI: 10.1016/j.phytol.2010.11.006
[45]	Niu Y, Wang R, Pu L, Zhang Y 2019 Dyes Pigm. 170 107594 DOI: 10.1016/j.dyepig.2019.107594
[46]	Bultinck P, Alsenoy C, Ayers P, Carbo-Dorca R 2007 J. Chem. Phys. 126 144111 DOI: 10.1063/1.2715563
[47]	Geldof D, Krishtal A, Blockhuys F, Alsenoy C 2011 J. Chem. Theory Comput. 7 1328 DOI: 10.1021/ct100743h
[48]	Verstraelen T, Ayers P, Speybroeck V, Waroquier M 2013 J. Chem. Theory Comput. 9 2221 DOI: 10.1021/ct4000923
[49]	Zhao J, Yao H, Liu J, Hoffmann M 2015 J. Phys. Chem. A 119 681 DOI: 10.1021/jp5120459
[50]	Zhou L, Liu J, Zhao G, Shi Y, Peng X, Han K 2007 Chem. Phys. 333 179 DOI: 10.1016/j.chemphys.2007.01.019
[51]	Rocard J, Berezin A, Leo F, Bonifazi D 2015 Angew. Chem. Int. Ed. 54 15739 DOI: 10.1002/anie.201507186
[52]	Zhao J, Li P 2015 RSC Adv. 5 73619 DOI: 10.1039/C5RA14601A
[53]	Moorthy J, Natarajan P, Venkatakrishnan, Huang D, Chow T 2007 Org. Lett. 9 5215 DOI: 10.1021/ol7023136
[54]	Zhao G, Northrop B, Stang P, Han K 2010 J. Phys. Chem. A 114 3418 DOI: 10.1021/jp911597z
[55]	Garo F, Haner R 2012 Angew. Chem. Int. Ed. 51 916 DOI: 10.1002/anie.201103295
[56]	Nakazato T, Kamatsuka T, Inoue J, Sakurai T, Seki S, Shinokubo H, Miyake Y 2018 Chem. Commun. 54 5177 DOI: 10.1039/C8CC01937A
[57]	Wang Y, Jia M, Zhang Q, Song X, Yang D 2019 Chin. Phys. B 28 103105 DOI: 10.1088/1674-1056/ab4042
[58]	Zhao G, Northrop B, Han K, Stang P 2010 J. Phys. Chem. A 114 9007 DOI: 10.1021/jp105009t
[59]	Zhao G, Chen R, Sun M, Liu J, Li G, Gao Y, Han K, Yang X, Sun L 2008 Chem. Eur. J. 14 6935 DOI: 10.1002/chem.200701868
[60]	Yin H, Zhang Y, Zhao H, Yang G, Shi Y, Zhang S, Ding D 2018 Dyes Pigm. 159 506 DOI: 10.1016/j.dyepig.2018.07.032
[61]	Han J, Liu X, Sun C, Li Y, Yin H, Shi Y 2018 RSC Adv. 8 29589 DOI: 10.1039/C8RA05812A
[62]	Li H, Han J, Zhao H, Liu X, Luo Y, Shi Y, Liu C, Jin M, Ding D 2019 J. Phys. Chem. Lett. 10 748 DOI: 10.1021/acs.jpclett.9b00026
[63]	Fan G, Han K, He G 2013 Chin. J. Chem. Phys. 26 635 DOI: 10.1063/1674-0068/26/06/635-645
[64]	Cong L, Yin H, Shi Y, Jin M, Ding D 2015 RSC Adv. 5 1205 DOI: 10.1039/C4RA09773D
[65]	Li H, Han J, Zhao H, Liu X, Ma L, Sun C, Yin H, Shi Y 2018 J. Clust. Sci. 29 585 DOI: 10.1007/s10876-018-1371-9
[66]	Merrick J, Moran D, Radom L 2007 J. Phys. Chem. A 111 11683 DOI: 10.1021/jp073974n
[67]	Palafox M, Talaya J, Guerrero-Martinez A, Tardajos G, Kumar H, Vats J, Rastogi V 2010 Spectrosc. Lett. 43 51 DOI: 10.1080/00387010903261149
[68]	Zhao J, Dong H, Yang H, Zheng Y 2019 ACS Appl. Bio. Mater 2 2060 DOI: 10.1021/acsabm.9b00088
[69]	Zhang M, Zhou Q, Zhang M, Dai Y, Song P, Jiang Y 2017 J. Clust. Sci. 28 1191 DOI: 10.1007/s10876-016-1122-8
[70]	Qu R, Zhang Q, Zhang X, Wang Z 2012 Spectrosc. Lett. 45 240 DOI: 10.1080/00387010.2011.607206
[71]	Tang K, Chang M, Lin T, Pan H, Fang T, Chen K, Hung W, Hsu Y, Chou P 2011 J. Am. Chem. Soc. 133 17738 DOI: 10.1021/ja2062693
[72]	Chou P, Wei C, Wu G, Chen W 1999 J. Am. Chem. Soc. 121 12186 DOI: 10.1021/ja9917619
[73]	Hsieh C, Chou P, Shih C, Chuang W, Chung M, Lee J, Joo T 2011 J. Am. Chem. Soc. 133 2932 DOI: 10.1021/ja107945m
[74]	Tseng H, Liu J, Chen Y, Chao C, Liu K, Chen C, Lin T, Hung C, Chou Y, Lin T, Wang T, Chou O 2015 J. Phys. Chem. Lett. 6 1477 DOI: 10.1021/acs.jpclett.5b00423
[75]	Wang J, Chu Q, Liu X, Wesdemiotis C, Pang Y 2013 J. Phys. Chem. B 117 4127 DOI: 10.1021/jp401612u
[76]	Wang J, Liu X, Pang Y 2014 J. Mater. Chem. B 2 6634 DOI: 10.1039/C4TB01109K
[77]	McDonald L, Liu B, Taraboletti A, Whiddon K, Shriver L, Konopka M, Liu Q, Pang Y 2016 J. Mater. Chem. B 4 7902 DOI: 10.1039/C6TB02456D
[78]	Wang J, Chen W, Liu X, Wesdemiotis C, Pang Y 2014 J. Mater. Chem. B 2 3349 DOI: 10.1039/c4tb00020j

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[1]	CAI XIAO-HONG, SHEN ZI-YONG, CHEN XI-MENG, LIU ZHAO-YUAN, MA XIN-WEN, LIU HUI-PING, HOU MING-DONG. THE MULTIPLE IONIZATION OF ARGON INDUCED BY PARTIALLY STRIPPED CARBON IONS[J]. Acta Phys. Sin. (Overseas Edition), 1997, 6(1): 6 -12 .
[2]	Li Xue-Chen, Liu Zhi-Hui, Jia Peng-Ying, Li Li-Chun, Yin Zeng-Qian, Dong Li-Fang. Study on the transition from filamentary discharge to diffuse discharge by using a dielectric barrier surface discharge device[J]. Chin. Phys., 2007, 16(10): 3016 -3021 .
[3]	Liu Chong-Xin. A new hyperchaotic dynamical system[J]. Chin. Phys., 2007, 16(11): 3279 -3284 .
[4]	Zhang Guo-Feng, Liu Jia. Entanglement in a generalized Jaynes--Cummings model[J]. Chin. Phys., 2007, 16(12): 3595 -3600 .
[5]	Wu Chun-Ya, Li Xue-Dong, Zhao Shu-Yun, Li Juan, Meng Zhi-Guo, Xiong Shao-Zhen, Zhang Fang. Solution-based metal induced crystallization of a-Si[J]. Chin. Phys. B, 2009, 18(3): 1237 -1241 .
[6]	Wang Liang-Ji, Zhang Shu-Ming, Zhu Ji-Hong, ZhuJian-Jun, Zhao De-Gang, Liu Zong-Shun, Jiang De-Sheng, WangYu-Tian, Yang Hui. Effect of surface treatment of GaN based light emitting diode wafers on the leakage current of light emitting diode devices[J]. Chin. Phys. B, 2010, 19(1): 17307 -017307 .
[7]	Sun Xiao-Juan, Lu Qi-Shao. Spatial coherence resonance induced by coloured noise and parameter diversity in a neuronal network[J]. Chin. Phys. B, 2010, 19(4): 40504 -040504 .
[8]	Wang Ke-Dong, Duan Kun-Jie, Liu Yu-Fang. Methyl orbital signatures in 2-amino-1-propanol[J]. Chin. Phys. B, 2012, 21(7): 73103 -073103 .
[9]	Gong Yong-Wang, Song Yu-Rong, Jiang Guo-Ping. Global dynamics of a novel multi-group model for computer worms[J]. Chin. Phys. B, 2013, 22(4): 40204 -040204 .
[10]	Zhou Ren-Lai, Ju You-Lun, Zhao Jie, Yang Chao,Wang Yue-Zhu. A theoretical and experimental investigation of an in-band pumped gain-switched thulium-doped fiber laser [J]. Chin. Phys. B, 2013, 22(6): 64208 -064208 .

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