Citation:
LIU Xiao-Jun, WANG Ning, CHENG Hao. Local and Long-Range Hybrid Density Functional Study on an Organic Light-Emitting Molecule with Pull-Push Structure[J]. Acta Physico-Chimica Sinica,
;2011, 27(07): 1640-1646.
doi:
10.3866/PKU.WHXB20110718
-
The absorption and fluorescence spectra of 3-(dicyanomethylene)-5,5-dimethyl-1-(4-[9- carbazol]-styryl)cyclohexene (DCDCC), an organic light emitting material with pull-push structure, were investigated using a time-dependent density functional theory (TD-DFT) approach and bulk solvent effects were taken into account. The performance of eight exchange-correlation functionals including both local and long-range hybrids was assessed by comparing the calculated electron transition energies to experimental observations. It turns out that the appropriate choice of functionals is crucial to obtain an accurate value and BMK hybrids, which contain 44% Hartree Fock exchange, in the frame of DFT and TD-DFT with the polarizable continuum model and a medium sized basis set, emerges as an effective strategy for DCDCC. Moreover, the planar and twisted intramolecular charge transfer (PICT and TICT) models were used to interpret the excited state structure of DCDCC although the charge transfer character of the excited-state was not as intense as to emit obvious double fluorescence. The accurate structures were optimized by BMK and supported the PICT model.
-
-
-
[1]
(1) Ju, H. D.;Wan, Y.; Yu,W. T.; Liu, A. Y.; Liu, Y.; Ren, Y.; Tao, X. T.; Zou, D. C. Thin Solid Films 2006, 515, 2403.
-
[2]
(2) Zachariasse, K. A.; Druzhinin, S. I.; Bosch,W.; Machinek, R. J. Am. Chem. Soc. 2004, 126, 1705.
- [3]
-
[4]
(4) Zhao, G.; Chen, R.; Sun, M.; Liu, J.; Li, G.; Gao, Y.; Han, K.; Yang, X.; Sun, L. Chem. Eur. J. 2008, 14, 6935.
- [5]
-
[6]
(6) Grabowski, Z. R.; Rotkiewicz, K.; Siemiarczuk, A.; Cowley, D. J.; Baumann,W. Nouv. J. Chim. 1979, 3, 443.
- [7]
- [8]
-
[9]
(9) Guido, C. A.; Mennucci, B.; Jacquemin, D.; Adamo, C. Phys. Chem. Chem. Phys. 2010, 12, 8016.
-
[10]
(10) Furche, F.; Ahlrichs, R. J. Chem. Phys. 2002, 117, 7433.
-
[11]
(11) Scalmani, G.; Frisch, M. J.; Mennucci, B.; Tomasi, J.; Cammi, R.; Barone, V. J. Chem. Phys. 2006, 124.
-
[12]
(12) Barone, V.; Improta, R.; Rega, N. Accounts Chem. Res. 2008, 41, 605.
-
[13]
(13) Jacquemin, D.; Wathelet, V.; Perpete, E. A.; Adamo, C. J. Chem. Theory Comput. 2009, 5, 2420.
-
[14]
(14) Jacquemin, D.; Perpete, E. A.; Ciofini, I.; Adamo, C. Accounts Chem. Res. 2009, 42, 326.
-
[15]
(15) Amat, A.; Clementi, C.; De Angelis, F.; Sgamellotti, A.; Fantacci, S. J. Phys. Chem. A 2009, 113, 15118.
-
[16]
(16) Lee, C.; Yang,W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
-
[17]
(17) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
- [18]
-
[19]
(19) Ernzerhof, M.; Scuseria, G. E. J. Chem. Phys. 1999, 110, 5029.
-
[20]
(20) Adamo, C.; Scuseria, G. E.; Barone, V. J. Chem. Phys. 1999, 111, 2889.
-
[21]
(21) Andzelm, J.; Rinderspacher, B. C.; Rawlett, A.; Dougherty, J.; Baer, R.; vind, N. J. Chem. Theory Comput. 2009, 5, 2835.
-
[22]
(22) Plotner, J.; Tozer, D. J.; Dreuw, A. J. Chem. Theory Comput. 2010, 6, 2315.
- [23]
-
[24]
(24) Dreuw, A.; Head- rdon, M. J. Am. Chem. Soc. 2004, 126, 4007.
-
[25]
(25) Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393, 51.
-
[26]
(26) Chai, J. D.; Head- rdon, M. J. Chem. Phys. 2008, 128, 84106.
-
[27]
(27) Chai, J. D.; Head- rdon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615.
-
[28]
(28) Zhao, Y.; Truhlar, D. Theor. Chem. Acc. 2008, 120, 215.
-
[29]
(29) Jacquemin, D.; Perpete, E. A.; Scuseria, G. E.; Ciofini, I.; Adamo, C. J. Chem. Theory Comput. 2008, 4, 123.
-
[30]
(30) Boese, A. D.; Martin, J. M. L. J. Chem. Phys. 2004, 121, 3405.
- [31]
-
[32]
(32) Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
-
[33]
(33) Ju, H. D. Design, Synthesis and Properties of Isophorone-based Light-emitting Materials. Ph. D. Dissertation, Shandong University, Jinan, 2007. [鞠海东. 异佛乐酮类发光材料的设计、合成与性质研究[D]. 济南: 山东大学, 2007.]
-
[34]
(34) Cammi, R.; Cossi, M.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1996, 105, 10556.
-
[35]
(35) Cammi, R.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1996, 104, 4611.
-
[36]
(36) Petersson, G. A.; Bennett, A.; Tensfeldt, T. G.; Al-Laham, M. A.; Shirley,W. A.; Mantzaris, J. J. Chem. Phys. 1988, 89, 2193.
-
[37]
(37) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
-
[38]
(38) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 09, Revision A.02; Gaussian, Inc.:Wallingford CT, 2009.
-
[39]
(39) Le Bahers, T.; Pauporte, T.; Scalmani, G.; Adamo, C.; Ciofini, I. Phys. Chem. Chem. Phys. 2009, 11, 11276.
-
[40]
(40) Stsiapura, V. I.; Maskevich, A. A.; Kuzmitsky, V. A.; Turoverov, K. K.; Kuznetsova, I. M. J. Phys. Chem. A 2007, 111, 4829.
-
[1]
-
-
-
[1]
Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
-
[2]
Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N4 site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
-
[3]
Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
-
[4]
Yue Wu , Jun Li , Bo Zhang , Yan Yang , Haibo Li , Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028
-
[5]
Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
-
[6]
Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
-
[7]
You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H2O2及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
-
[8]
Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
-
[9]
Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
-
[10]
Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
-
[11]
Hui Li , Jia Nie , Zhongyuan Lü , Hujun Qian , Youliang Zhu , Fuquan Bai , Zexing Qu , Ronglin Zhong . Developing a Lecture Mode for Theoretical and Computational Chemistry Curriculum under the “Modernization of Chinese Education” Initiative. University Chemistry, 2025, 40(3): 1-9. doi: 10.3866/PKU.DXHX202402007
-
[12]
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
-
[13]
Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
-
[14]
Lijun Huo , Mingcun Wang , Tianyi Zhao , Mingjie Liu . Exploration of Undergraduate and Graduate Integrated Teaching in Polymer Chemistry with Aerospace Characteristics. University Chemistry, 2024, 39(6): 103-111. doi: 10.3866/PKU.DXHX202312059
-
[15]
Xinghai Liu , Hongke Wu . Exploration and Practice of Ideological and Political Education in Heterocyclic Chemistry Based on "Fentanyl" Event. University Chemistry, 2024, 39(8): 359-364. doi: 10.3866/PKU.DXHX202312100
-
[16]
Hongsheng Tang , Yonghe Zhang , Dexiang Wang , Xiaohui Ning , Tianlong Zhang , Yan Li , Hua Li . A Wonderful Journey through the Kingdom of Hazardous Chemicals. University Chemistry, 2024, 39(9): 196-202. doi: 10.12461/PKU.DXHX202403098
-
[17]
Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
-
[18]
Jia Yao , Xiaogang Peng . Theory of Macroscopic Molecular Systems: Theoretical Framework of the Physical Chemistry Course in the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 27-37. doi: 10.12461/PKU.DXHX202408117
-
[19]
Yanxin Wang , Hongjuan Wang , Yuren Shi , Yunxia Yang . Application of Python for Visualizing in Structural Chemistry Teaching. University Chemistry, 2024, 39(3): 108-117. doi: 10.3866/PKU.DXHX202306005
-
[20]
Yongming Guo , Jie Li , Chaoyong Liu . Green Improvement and Educational Design in the Synthesis and Characterization of Silver Nanoparticles. University Chemistry, 2024, 39(3): 258-265. doi: 10.3866/PKU.DXHX202309057
-
[1]
Metrics
- PDF Downloads(1086)
- Abstract views(2760)
- HTML views(5)