Please wait a minute...
Chin. Phys. B, 2019, Vol. 28(1): 018201    DOI: 10.1088/1674-1056/28/1/018201
INTERDISCIPLINARY PHYSICS AND RELATED AREAS OF SCIENCE AND TECHNOLOGY Prev   Next  

Exploring the effect of aggregation-induced emission on the excited state intramolecular proton transfer for a bis-imine derivative by quantum mechanics and our own n-layered integrated molecular orbital and molecular mechanics calculations

Huifang Zhao(赵慧芳), Chaofan Sun(孙朝范), Xiaochun Liu(刘晓春), Hang Yin(尹航), Ying Shi(石英)
Institute of Atomic and Molecular Physics, Jilin University, Changchun 130012, China
Abstract  

We theoretically investigate the excited state intramolecular proton transfer (ESIPT) behavior of the novel fluorophore bis-imine derivative molecule HNP which was designed based on the intersection of 1-(hydrazonomethyl)-naphthalene-2-ol and 1-pyrenecarboxaldehyde. Especially, the density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods for HNP monomer are introduced. Moreover, the “our own n-layered integrated molecular orbital and molecular mechanics” (ONIOM) method (TDDFT:universal force field (UFF)) is used to reveal the aggregation-induced emission (AIE) effect on the ESIPT process for HNP in crystal. Our results confirm that the ESIPT process happens upon the photoexcitation for the HNP monomer and HNP in crystal, which is distinctly monitored by the optimized geometric structures and the potential energy curves. In addition, the results of potential energy curves reveal that the ESIPT process in HNP will be promoted by the AIE effect. Furthermore, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) for the HNP monomer and HNP in crystal have been calculated. The calculation demonstrates that the electron density decrease of proton donor caused by excitation promotes the ESIPT process. In addition, we find that the variation of atomic dipole moment corrected Hirshfeld population (ADCH) charge for proton acceptor induced by the AIE effect facilitates the ESIPT process. The results will be expected to deepen the understanding of ESIPT dynamics for luminophore under the AIE effect and provide insight into future design of high-efficient AIE compounds.

Keywords:  time-dependent density functional theory (TDDFT) method      excited state intramolecular proton transfer (ESIPT)      our own n-layered integrated molecular orbital and molecular mechanics (ONIOM) method      potential energy curves      atomic dipole moment corrected Hirshfeld population (ADCH) charge  
Received:  19 October 2018      Revised:  09 November 2018      Accepted manuscript online: 
PACS:  82.39.Jn (Charge (electron, proton) transfer in biological systems)  
  31.15.ee (Time-dependent density functional theory)  
  87.15.ht (Ultrafast dynamics; charge transfer)  
Fund: 

Project supported by the National Natural Science Foundation of China (Grant Nos. 11574115 and 11704146).

Corresponding Authors:  Hang Yin, Ying Shi     E-mail:  yinhang@jlu.edu.cn;shi_ying@jlu.edu.cn

Cite this article: 

Huifang Zhao(赵慧芳), Chaofan Sun(孙朝范), Xiaochun Liu(刘晓春), Hang Yin(尹航), Ying Shi(石英) Exploring the effect of aggregation-induced emission on the excited state intramolecular proton transfer for a bis-imine derivative by quantum mechanics and our own n-layered integrated molecular orbital and molecular mechanics calculations 2019 Chin. Phys. B 28 018201

[1] Weller A 1956 Ber. Bunsenges. Phys. Chem. 60 1144
[2] Zheng D Y, Zhang M Z and Zhao G J 2017 Sci. Rep. 7 13766
[3] Shynkar V V, Klymchenko A S, Kunzelmann C, Duportail G, Muller C D, Demchenko A P, Freyssinet J M and Mely Y 2007 J. Am. Chem. Soc. 129 2187
[4] Tang K C, Chang M J, Lin T Y, Pan H A, Fang T C, Chen K Y, Hung W Y, Hsu Y H and Chou P T 2011 J. Am. Chem. Soc. 133 17738
[5] Zhao J Z, Ji S M, Chen Y H, Guo H M and Yang P 2012 Phys. Chem. Chem. Phys. 14 8803
[6] Shiraishi Y, Matsunaga Y, Hongpitakpong P and Hirai T 2013 Chem. Commun. 49 3434
[7] Liu B, Wang H, Wang T S, Bao Y Y, Du F F, Tian J, Li Q B A and Bai R K 2012 Chem. Commun. 48 2867
[8] Demchenko A P, Tang K C and Chou P T 2013 Chem. Soc. Rev. 42 1379
[9] Klymchenko A S 2017 Acc. Chem. Res. 50 366
[10] Cheng X, Wang K, Huang S, Zhang H Y, Zhang H Y and Wang Y 2015 Angew. Chem. Int. Ed. 54 8369
[11] Zhang M X, Zhou Q, Zhang M R, Dai Y M, Song P and Jiang Y 2017 J. Cluster Sci. 28 1191
[12] Jia X L, Li C Z, Li D L and Liu Y F 2018 Spectrochim. Acta Part. A 192 168
[13] Han K L and Zhao G J 2011 Hydrogen Bonding Transfer in the Excited State (Chichester: John Wiley & Sons) p. 555
[14] Wu W R 2015 J. Phys. Org. Chem. 28 596
[15] Yang D P, Zheng R, Wang Y S and Lv J 2016 J. Phys. Org. Chem. 29 161
[16] Yang D P, Yang G, Zhao J F, Song N H, Zheng R and Wang Y S 2018 J. Phys. Org. Chem. 31 e3729
[17] Sen Gupta S K 2016 J. Phys. Org. Chem. 29 251
[18] Yang D P, Yang G, Zhao J F, Zheng R, Wang Y S and Lv J 2017 J. Phys. Org. Chem. 30 e3684
[19] Padalkar V S and Seki S 2016 Chem. Soc. Rev. 45 169
[20] Mei J, Leung N L C, Kwok R T K, Lam J W Y and Tang B Z 2015 Chem. Rev. 115 11718
[21] Kumbhar H S and Shankarling G S 2015 Dyes Pigm. 122 85
[22] Shreykar M R and Sekar N 2017 J. Fluoresc. 27 1687
[23] Hong Y, Lam J W Y and Tang B Z 2009 Chem. Commun. 4332
[24] Dwivedi B K, Singh V D, Paitandi R P and Pandey D S 2018 Chem. Phys. Chem. 19 2672
[25] Samanta S, Manna U and Das G 2017 New J. Chem. 41 1064
[26] Samanta S, Goswami S, Hoque M N, Ramesh A and Das G 2014 Chem. Commun. 50 11833
[27] Winnik F M 1993 Chem. Rev. 93 587
[28] Sahoo D, Narayanaswami V, Kay C M and Ryan R O 2000 Biochemistry 39 6594
[29] Chung L W, Sameera W M C, Ramozzi R, Page A J, Hatanaka M, Petrova G P, Harris T V, Li X, Ke Z F, Liu F Y, Li H B, Ding L N and Morokuma K 2015 Chem. Rev. 115 5678
[30] Dapprich S, Komáromi I, Byun K S, Morokum K and Frisch M J 1999 J. Mol. Struct. THEOCHEM 461 1
[31] Vreven T, Morokuma K, Farkas Ö Schlegel H B and Frisch M J 2003 J. Comput. Chem. 24 760
[32] Yang D P, Yang Y G and Liu Y F 2014 Spectrochim. Acta Part. A 117 379
[33] Song P, Li Y Z, Ma F C, Pullerits T and Sun M T 2013 J. Phys. Chem. C 117 15879
[34] Yin H and Shi Y 2018 Chin. Phys. B 27 058201
[35] Zhao G J and Han K L 2007 J. Phys. Chem. A 111 2469
[36] Zhao G J and Han K L 2012 Acc. Chem. Res. 45 404
[37] Yin H, Shi Y and Wang Y 2014 Spectrochim. Acta Part. A 129 280
[38] Yin H, Li H, Xia G M, Ruan C Y, Shi Y, Wang H M, Jin M X and Ding D J 2016 Sci. Rep. 6 19774
[39] Li C Z, Ma C, Li D L and Liu Y F 2016 J. Lumin. 172 29
[40] Xu B B, Li Y Z, Song P, Ma F C and Sun M T 2017 Sci. Rep. 7 45688
[41] Furche F and Ahlrichs R 2002 J. Chem. Phys. 117 7433
[42] Li H, Ma L N, Yin H and Shi Y 2018 Chin. Phys. B 27 098201
[43] Feller D 1996 J. Comput. Chem. 17 1571
[44] Rappe A K, Casewit C J, Colwell K S, Goddard W A and Skiff W M 1992 J. Am. Chem. Soc. 114 10024
[45] Rappe A K and Goddard W A 1991 J. Phys. Chem. 95 3358
[46] Wang B, Wang X J, Wang W L and Liu F Y 2016 J. Phys. Chem. C 120 21850
[47] Vreven T, Byun K S, Komáromi I, Dapprich S, Montgomery Jr J A, Morokuma K and Frisch M J 2006 J. Chem. Theory Comput. 2 815
[48] Frisch M J et al. 2009 Gaussian 09 Revision B.01 (Gaussian, Inc., Wallingford)
[49] Lu T and Chen F W 2012 J. Comput. Chem. 33 580
[50] Zhou P W and Han K L 2018 Acc. Chem. Res. 51 1681
[1] Highly accurate theoretical study on spectroscopic properties of SH including spin-orbit coupling
Shu-Tao Zhao(赵书涛), Xin-Peng Liu(刘鑫鹏), Rui Li(李瑞), Hui-Jie Guo(国慧杰), and Bing Yan(闫冰). Chin. Phys. B, 2021, 30(7): 073104.
[2] Configuration interaction study on low-lying states of AlCl molecule
Xiao-Ying Ren(任笑影), Zhi-Yu Xiao(肖志宇), Yong Liu(刘勇), and Bing Yan(闫冰). Chin. Phys. B, 2021, 30(5): 053101.
[3] Exploration and elaboration of photo-induced proton transfer dynamical mechanism for novel 2-[1,3]dithian-2-yl-6-(7aH-indol-2-yl)-phenol sensor
Lei Xu(许磊), Tian-Jie Zhang(张天杰), Qiao-Li Zhang(张巧丽), Da-Peng Yang(杨大鹏). Chin. Phys. B, 2020, 29(5): 053102.
[4] The substituent effect on the excited state intramolecular proton transfer of 3-hydroxychromone
Yuzhi Song(宋玉志), Songsong Liu(刘松松), Jiajun Lu(陆佳骏), Hui Zhang(张慧), Changzhe Zhang(张常哲), Jun Du(杜军). Chin. Phys. B, 2019, 28(9): 093102.
[5] Low-lying electronic states of aluminum monoiodide
Xiang Yuan(袁翔), Shuang Yin(阴爽), Yi Lian(连艺), Pei-Yuan Yan(颜培源), Hai-Feng Xu(徐海峰), Bing Yan(闫冰). Chin. Phys. B, 2019, 28(4): 043101.
[6] Potential energy curves, transition dipole moments, and radiative lifetimes of KBe molecule
Ming-Jie Wan(万明杰), Cheng-Guo Jin(金成国), You Yu(虞游), Duo-Hui Huang(黄多辉), Ju-Xiang Shao(邵菊香). Chin. Phys. B, 2017, 26(3): 033101.
[7] MRCI+Q study of the low-lying electronic states of CdF including spin—orbit coupling
Shu-Tao Zhao(赵书涛), Bing Yan(闫冰), Rui Li(李瑞), Shan Wu(武山), Qiu-Ling Wang(王秋玲). Chin. Phys. B, 2017, 26(2): 023105.
[8] Ab initio investigation of sulfur monofluoride and its singly charged cation and anion in their ground electronic state
Song Li(李松), Shan-Jun Chen(陈善俊), Yan Chen(陈艳), Peng Chen(陈朋). Chin. Phys. B, 2016, 25(3): 033101.
[9] Low-lying electronic states of CuN calculated by MRCI method
Shu-Dong Zhang(张树东), Chao Liu(刘超). Chin. Phys. B, 2016, 25(10): 103103.
[10] Potential energy curves and spectroscopic properties of X2Σ+ and A2Π states of 13C14N
Liao Jian-Wen (廖建文), Yang Chuan-Lu (杨传路). Chin. Phys. B, 2014, 23(7): 073401.
[11] Ab initio MRCI+Q study on potential energy curves and spectroscopic parameters of low-lying electronic states of CS+
Li Rui (李瑞), Wei Chang-Li (魏长立), Sun Qi-Xiang (孙启响), Sun Er-Ping (孙二平), Jin Ming-Xing (金明星), Xu Hai-Feng (徐海峰), Yan Bing (闫冰). Chin. Phys. B, 2013, 22(12): 123103.
[12] Further investigations of the low-lying electronic states of AsO+ radical
Zhu Zun-Lue (朱遵略), Qiao Hao (乔浩), Lang Jian-Hua (郎建华), Sun Jin-Feng (孙金锋). Chin. Phys. B, 2013, 22(10): 103102.
[13] Theoretical study of potential energy curves, spectroscopic constants, and radiative lifetimes of low-lying states in SeO molecule
Li Rui (李瑞), Lian Ke-Yan (连科研), Li Qi-Nan (李奇楠), Miao Feng-Juan (苗凤娟), Yan Bing (闫冰), Jin Ming-Xing (金明星). Chin. Phys. B, 2012, 21(12): 123102.
[14] Accurate ab initio study of low-lying electronic states of phosphorus nitride radical
Wang Jie-Min(王杰敏), Sun Jin-Feng(孙金锋), and Shi De-Heng(施德恒). Chin. Phys. B, 2010, 19(11): 113404.
[15] Spin--orbit ab initio curves of 80Se2+ ion and theassignment of photoelectron spectra of 80Se2 molecule
Yan Bing(闫冰), Pan Shou-Fu(潘守甫), and Guo Qing-Qun(郭庆群). Chin. Phys. B, 2008, 17(9): 3318-3321.
No Suggested Reading articles found!