取代基对3(5)-(9-蒽基)吡唑光学性质的影响

doi:10.3866/PKU.WHXB20110303

Abstract

Abstract:

The ground state (S₀) structures of 3(5)-(9-anthryl) pyrazole and its derivatives were obtained using the density functional theory (DFT) B3LYP/6-31G(d) method. The first singlet excited state (S₁) structures were optimized using the singlet-excitation configuration interaction (CIS)/6-31G(d) method. The absorption and emission spectra were then evaluated using the time-dependent density functional theory (TD-DFT) B3LYP method with the 6-311++G(d,p) basis set. Our calculation results reveal that for all the derivatives (electron-withdrawing groups or electron-donating groups) the calculated absorption and fluorescence emission wavelength values all show red shifts compared with the parent 3(5)-(9-anthryl) pyrazole. We also find that compared with the parent 3(5)-(9-anthryl) pyrazole, the derivatives with ―R=―BH₂, ―CCl₃, ―CHO, ―NH₂ are good candidates for longer absorption wavelength materials and for longer fluorescence emission wavelength materials.

Key words: Absorption spectrum, Fluorescence emission spectrum, 3(5)-(9-Anthryl) pyrazole, Excited state

WANG Kun-Peng, WANG Chang-Sheng. Effect of Substituents on the Optical Properties of 3(5)-(9-Anthryl) Pyrazole[J]. Acta Phys. -Chim. Sin. 2011, 27(03), 589-594. doi: 10.3866/PKU.WHXB20110303

References

(1) Mizukami, S.; Houjou, H.; Sugaya, K.; Koyama, E.; Tokuhisa, H.; Sasaki, T.; Kanesato, M. Chem. Mater. 2005, 17, 50.
(2) Bader, M. M.; Custelcean, R.; Ward, M. D. Chem. Mater. 2003, 15, 616.
(3) Wakamiya, A.; Ide, T.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 14859.
(4) Murata, H.; Kafafi, Z. H.; Uchida, M. Appl. Phys. Lett. 2002, 80, 189.
(5) Chen, J.; Law, C. C. W.; Lam, J. W. Y.; Dong, Y.; Lo, S. M. F.; Williams, I. D.; Zhu, D.; Tang, B. Z. Chem. Mater. 2003, 15, 1535.
(6) Sapochak, L. S.; Benincasa, F. E.; Schofield, R. S.; Baker, J. L.; Riccio, K. K. C.; Fogarty, D.; Kohlmann, H.; Ferris, K. F.; Burrows, P. E. J. Am. Chem. Soc. 2002, 124, 6119.
(7) Brinkmann, M.; Gadret, G.; Muccini, M.; Taliani, C.; Masciocchi, N.; Sironi. A. J. Am. Chem. Soc. 2000, 122, 5147.
(8) Halls, M. D.; Schlegel, H. B. Chem. Mater. 2001, 13, 2632.
(9) Geng, W. T.; Oda, M.; Nara, J.; Kondo, H.; Ohno, T. J. Phys. Chem. B 2008, 112, 2795.
(10) Shi, L.; Hong, B.; Guan, W.; Wu, Z.; Su, Z. J. Phys. Chem. A 2010, 114, 6559.
(11) Hu, B.; Gahungu, G.; Zhang, J. J. Phys. Chem. A 2007, 111, 4965.
(12) Sun, M.; Niu, B.; Zhang, J. Theor. Chem. Acc. 2008, 119, 489.
(13) Fan, Y.; Zhao, Y.; Ye, L.; Li, B.; Yang, G.; Wang, Y. Crystal Growth & Design 2009, 9, 1421.
(14) Fan, Y.; Song, W.; Yu, D.; Ye, K.; Zhang, J.; Wang, Y. CrystEngComm 2009, 11, 1716.
(15) Gaal, M.; Gadermaier, C.; Plank, H.; Moderegger, E.; Pogantsch,A.; Leising, G.; List, E. J. W. Adv. Mater. 2003, 15, 1165.
(16) Zhao, Y.; Gao, H.; Fan, Y.; Zhuo, T.; Su, Z.; Liu, Y.; Wang, Y. Adv. Mater. 2009, 21, 3165.
(17) Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477.
(18) Chen, Y.; Au, J.; Kazlas, P.; Ritenour, A.; Gates, H.; McCreary, M. Nature 2003, 423, 136.
(19) Rakow, N. A; Suslick, K. S. Nature 2000, 406, 710.
(20) Zhang, H.; Zhang, Z.; Ye, K.; Zhang, J.; Wang, Y. Adv. Mater. 2006, 18, 2369.
(21) Gao, L.; Lu, N.; Hao, J.; Hu, W.; Wang, W.; Wu, Y.; Wang, Y.; Chi, L. Langmuir 2008, 24, 12745.
(22) Gao, L.; Lu, N.; Hao, J.; Hu, W.; Shi, G.; Wang, Y.; Chi, L. Langmuir 2009, 25, 3894.
(23) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
(24) Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135.
(25) Cancès, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.

[1]	Yujie DONG,Chendong XU,Shizhao WANG,Weijun LI,Qingbao SONG,Cheng ZHANG. Stabilization of the E/Z Configuration for Cyanostilbene-based Luminogens by Enhanced Charge Transfer Excited State [J]. Acta Physico-Chimica Sinica, 2019, 35(6): 637-643.
[2]	Ágnes NAGY. Phase Space View of Ensembles of Excited States [J]. Acta Phys. -Chim. Sin., 2018, 34(5): 492-496.
[3]	Qian ZHU,Chao-Tun CAO,Chen-Zhong CAO. Extension and Application of Excited-State Constants of meta-Substituents [J]. Acta Phys. -Chim. Sin., 2017, 33(4): 729-735.
[4]	Jin SUN,Zong-Ling DING,Yuan-Qin YU,Guang LI. Absorption Spectra of Azobenzene Molecules on Au Nanoparticle Surface [J]. Acta Phys. -Chim. Sin., 2017, 33(11): 2199-2206.
[5]	Ying-Chun JIN,Xu-Ming ZHENG. UV Absorption and Resonance Raman Spectra of 2, 4-Dithiouracil [J]. Acta Physico-Chimica Sinica, 2017, 33(10): 1989-1997.
[6]	Hua-Bin CHEN,Xiao-Hui ZHANG,Li-Zhen GONG,Jing HE,Xuan XU,Zhi-Guang XU,Hai-Yang LIU. Effect of β-Substituents on the Electronic Absorption Spectra of Manganese(Ⅴ)-oxo Corrole Complexes [J]. Acta Phys. -Chim. Sin., 2016, 32(8): 1983-1989.
[7]	Lin YANG,Yang LI,Shu CHEN,Jing ZHANG,Min ZHANG,Peng WANG. Ultrafast Spectroscopic Studies of Excited State Relaxation and Electron Injection in Organic Dye-Sensitized Solar Cells [J]. Acta Phys. -Chim. Sin., 2016, 32(1): 329-336.
[8]	Ying-Na. CUI,Jing-Mei. YIN,Ying-Ping. JIA,Shen-Min. LI. Experimental and Density Functional Theoretical Studies on the Spectra of N, N'-di[3-hydroxy-4-(2-benzothiazole)phenyl]urea [J]. Acta Phys. -Chim. Sin., 2015, 31(9): 1647-1654.
[9]	Li-Mei. HOU,Zhi. WEN,Yin-Xiang. LI,Hua-You. HU,Yu-He. KAN,Zhong-Min. SU. Molecular Design of Indolizine Derivative as Sensitizers for Organic Dye-Sensitized Solar Cells [J]. Acta Phys. -Chim. Sin., 2015, 31(8): 1504-1512.
[10]	LI Hai-Xia, ZHOU Bao-Chang, LIU Yan-Cheng, TANG Rui-Zhi, ZHANG Peng, LI Jing-Ye, WANG Wen-Feng. Primary Photochemical Properties of Difloxacin in Neutral Aqueous Solution [J]. Acta Phys. -Chim. Sin., 2014, 30(11): 2134-2141.
[11]	ZHOU Dan-Hong, LI Miao-Miao, CUI Li-Li. Photophysical Properties and Photoinduced Electron Transfer Mechanism in a Near-IR Fluorescent Probe for Monitoring Peroxynitrite [J]. Acta Phys. -Chim. Sin., 2013, 29(07): 1453-1460.
[12]	SONG Hong-Juan, ZHANG Meng-Ying, SUN Xiu-Xin, SUN Shi-Ling QIU Yong-Qing. Nonlinear Optical Properties of a Series of 6,12-Diethynylindeno[1,2-b]fluorene Derivatives [J]. Acta Phys. -Chim. Sin., 2012, 28(12): 2839-2844.
[13]	YUAN Shuai, MA Jing, ZHANG Wen-Ying, SHU Kun-Xian, DOU Yu-Sheng. Semiclassical Dynamics Simulation and CASSCF Calculation for 5-Methyl Cytosine and Cytosine [J]. Acta Phys. -Chim. Sin., 2012, 28(12): 2803-2808.
[14]	LI Ying-Ruo, ZHANG Hong-Tao, QI Chuan-Min, GUO Xue-Feng. New Spiropyran Derivatives: Ion Sensing and Information Processing at the Molecular Level [J]. Acta Phys. -Chim. Sin., 2012, 28(10): 2471-2479.
[15]	LIANG Gui-Jie, ZHONG Zhi-Cheng, CHEN Mei-Hua, XU Jie, XU Wei-Lin, HE Ping, HOU Qiu-Fei, LI Zai-Fang. Effect of Donor Moieties on the Electronic Structures and Absorption Spectra of Indoline Dyes [J]. Acta Phys. -Chim. Sin., 2012, 28(08): 1885-1891.

Effect of Substituents on the Optical Properties of 3(5)-(9-Anthryl) Pyrazole

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0