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
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摘要
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.
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.
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.
引文
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[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
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[46]Wang B,Wang X J,Wang W L and Liu F Y 2016 J.Phys.Chem.C 12021850
[47]Vreven T,Byun K S,Komaromi 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
[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.421379
[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 2015Angew.Chem.Int.Ed.54 8369
[11]Zhang M X,Zhou Q,Zhang M R,Dai Y M,Song P and Jiang Y 2017J.Cluster Sci.28 1191
[12]Jia X L,Li C Z,Li D L and Liu Y F 2018 Spectrochim.Acta Part.A192 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.29161
[16]Yang D P,Yang G,Zhao J F,Song N H,Zheng R and Wang Y S 2018J.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 2015Chem.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,Komaromi I,Byun K S,Morokum K and Frisch M J 1999J.Mol.Struct.THEOCHEM 461 1
[31]Vreven T,Morokuma K,FarkasO Schlegel H B and Frisch M J 2003J.Comput.Chem.24 760
[32]Yang D P,Yang Y G and Liu Y F 2014 Spectrochim.Acta Part.A 117379
[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 M1992 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 12021850
[47]Vreven T,Byun K S,Komaromi 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