Theoretical study on twisted intramolecular charge transfer of 1-aminoanthraquinone in different solvents

doi:10.1088/1674-1056/27/8/083401

Abstract The twisted intramolecular charge transfer and the excited state relaxation of 1-aminoanthraquinone (1-NH₂-AQ) in different solvents are investigated using quantum chemical calculations in this paper. The geometries of the ground state are optimized both in gas and solvents based on the high-level ab initio calculations, the lowest excited singlet state geometry is optimized only in gas for simplicity. An intramolecular charge transfer property is substantiated by the large change of dipole moments between the S₀ and S₁ states. The mechanism of twisted intramolecular charge transfer is proposed by the conformational relaxation on the potential surface of the S₁ state. Quantum chemical calculations present that internal conversion and intersystem crossing are important approaches to the ultrafast deactivation of the S₁ state via the twisting of the amino group. The smaller energy difference between the S₀ and S₁ state shows that the internal conversion process is much faster in a polar solvent than in a nonpolar solvent. Energy intersections between the T₂ and S₁ state in cyclohexane and dioxane indicate a faster intersystem crossing process in them than in ethanol. These theoretical results agree well with the previous experimental results. Energy barriers are predicted on the potential surface of the S₁ state, and they have a positive correlation to solvent viscosity, and the timescale of twisted intra-molecular charge transfer in dioxane is predicted to be longer than in cyclohexane and ethanol.

Keywords: 1-aminoanthraquinone conformational relaxation twisted intra-molecular charge transfer quantum chemical calculations

Received: 02 April 2018
Revised: 11 May 2018
Accepted manuscript online:

PACS:	34.70.+e	(Charge transfer)
	31.70.Hq	(Time-dependent phenomena: excitation and relaxation processes, and reaction rates)
	33.15.Hp	(Barrier heights (internal rotation, inversion, rotational isomerism, conformational dynamics))
	32.70.Cs	(Oscillator strengths, lifetimes, transition moments)

Fund: Project supported by the Program of Outstanding Innovation Team of Hubei Normal University, China (Grant No. T201502), the Natural Science Foundation of Hubei Province, China (Grant Nos. 2014CFB349 and 2016CFC742), and the National Natural Science Foundation of China (Grant No. 11674355).

Corresponding Authors: Si-Mei Sun
E-mail: 15827610655@163.com

Cite this article:

Si-Mei Sun(孙四梅), Song Zhang(张嵩), Chao Jiang(江超), Xiao-Shan Guo(郭小珊), Yi-Hui Hu(胡义慧) Theoretical study on twisted intramolecular charge transfer of 1-aminoanthraquinone in different solvents 2018 Chin. Phys. B 27 083401

[1]	Marcaida I and Maguregui M et al. 2017 Anal. Bioanalytical Chem. 409 2221
[2]	Arba M and Tjahjono D H 2014 J. BioMol. Struct. Dyn. 33 657
[3]	Zhao P, Xu L, Huang J, Fu B, Yu H, Zhang W, Chen J, Yao J and Ji L 2008 Bioorg. Chem. 36 278
[4]	Carmieli R, et al. 2012 J. Am. Chem. Soc. 134 11251
[5]	Breslin D T, Coury J E, Anderson J R, Mcfail-Isom L, Kan Y, Williams L D, Bottomley L A and Schuster G B 1997 J. Am. Chem. Soc. 119 5043
[6]	Gao A, Deng W and Chen H 2011 Adv. Mater. Res. 148 1273
[7]	Yang G, Zhao S, Chen N and Li S 2016 Chem. Pharm. Bull. 64 1310
[8]	Al-Otaibi J S, Spittle P T and Gogary T M 2017 J. Mol. Struct. 1127 751
[9]	Lewis F D, Thazhathveetil A K, Zeidan T A, Vura-Weis J and Wasielewski R M 2010 J. Am. Chem. Soc. 132 444
[10]	Shao F W, Augustyn K and Barton J K 2005 J. Am. Chem. Soc. 127 17445
[11]	Jono R and Yamashita K 2011 J. Phys. Chem. C 116 1445
[12]	Kuang Z and He G 2018 J. Phys. Chem. C 122 3727
[13]	Tao M, Liu L, Liu D and Zhou X 2010 Dyes Pigments 85 21
[14]	Farztdinov V M, Schanz R, Kovalenko S A and Ernsting N P 2000 J. Phys. Chem. A 104 11486
[15]	Kovalenko S A, Schanz R, Farztdinov V M, Hennig H and Ernsting N P 2000 Chem. Phys. Lett. 323 312
[16]	Druzhinin S I, Ernsting N P, Kovalenko S A, Lustres L P, Senyushkina T A and Zachariasse K A 2006 J. Phys. Chem. A 110 2955
[17]	Rafiq S, Yadav R and Sen P 2011 J. Phys. Chem. A 115 8335
[18]	Ghosh R and Palit D K 2012 J. Phys. Chem. A 116 1993
[19]	Lippert E, Lüder W and Boos H 1962 in Advances in Molecular Spectroscopy; European Conference on Molecular Spectroscopy, Bologna, Italy, 1959; Mangini A, ed. (Oxford: Pergamon Press) p. 443
[20]	Rettig W 1986 Angew. Chem. Int. Ed. Eng. 25 971
[21]	Grabowski Z R, Rotkiewicz K and Rettig W 2003 Chem. Rev. 103 3899
[22]	Yoshihara T, Galievsky V A, Druzhinin S I, Saha S and Zachariasse K A 2003 Photochem. Photobiol. Sci. 2 342
[23]	Lee J, Fujiwara T, Kofron W G, Zgierski M Z and Lim E C 2008 J. Chem. Phys. 128 164512
[24]	Köhn A and Hättig C 2004 J. Am. Chem. Soc. 126 7399
[25]	Zachariasse K A, Yoshihara T and Druzhinin S I 2002 J. Phys. Chem. A 106 6325
[26]	Siemiarczuk A, Grabowski Z R, Krówczyński A, Asher M and Ottolenghi M 1977 Chem. Phys. Lett. 51 315
[27]	Gorse A and Pesquer M 1995 J. Phys. Chem. 99 4039
[28]	Sobolewski A L and Domcke W 1996 Chem. Phys. Lett. 250 428
[29]	Zachariasse K A and Kühnle W, et al. 1997 J. Photochem. Photobiol. A: Chem. 105 373
[30]	Rotkiewicz K, Grellmann K H and Grabowski Z R 1973 Chem. Phys. Lett. 19 315
[31]	Cornelissen-Gude C and Rettig W 1998 J. Phys. Chem. A 102 7754
[32]	Sobolewski A L, Sudholt W and Domcke W 1998 J. Phys. Chem. A 102 2716
[33]	Shi Q, Peng T and Wang S 2003 Chin. J. Anal. Chem. 31 1212
[34]	Sigman D S, Mazumder A and Perrin D M 1993 Chem. Rev. 93 2295
[35]	Armitage B, Yu C J, Devadoss C and Schuster G B 1994 J. Am. Chem. Soc. 116 9847
[36]	McKnight R E, Zhang J G and Dixon D W 2004 Bioorg. Med. Chem. Lett. 14 401
[37]	Chen N, Cheng S, Zhao S, Dong J, Gong P, Wang S and Li Z 2010 Chin. J. Organ. Chem. 30 1677
[38]	Carter T P, Van Benthem M H and Gillispie G D 1983 J. Phys. Chem. 87 1891
[39]	Balakrishnan N and Gillispie G D 1989 J. Phys. Chem. 93 2337
[40]	Srivatsavoy V J P, Venkataraman B and Periasamy N 1992 Proc. Indian Acad. Sci. 104 731
[41]	Inoue H, Hida M, Nakashima N and Yoshihara K 1982 J. Phys. Chem. 86 3184
[42]	Ghosh R and Palit D K 2013 Photochem. Photobiol. Sci. 12 987
[43]	Benlamari S, Bendjeddou H, Boulechfar R, Amara Korba S, Meradji H, Ahmed R, Ghemid S, Khenata R and Bin Omran S 2018 Chin. Phys. B 27 037104
[44]	Liu S, Ma Y, Yang Y, Liu S, Li Y, Song Y 2018 Chin. Phys. B 27 023103
[45]	Zhang Z, Zhang Y, Xue W, Jia W, Zhang C, Li C and Cui P 2017 Chin. Phys. B 26 123102
[46]	Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 09, Revision A.02, Gaussian, Inc.: Wallingford, CT, 2009
[47]	Christian M, Jörg S and Jürgen T 2006 J. Phys. Chem. B 110 19820
[48]	Zhang S, Sun S, Zhou M, Wang L and Zhang B 2017 Sci. Rep. 7 43419
[49]	Lister D G, Tyler J K, Hog J H and Larsen N W 1974 J. Mol. Struct. 23 253
[50]	Zaitsev B E, Preobrazhenskaya L B, Kolokolov B N and Allenov V M 1970 Russ. J. Phys. Chem. 44 1210
[51]	Marasinghe P A B and Gillispie G D 1989 Chem. Phys. 136 249

[1]	Effect of conical intersection of benzene on non-adiabatic dynamics Duo-Duo Li(李多多) and Song Zhang(张嵩). Chin. Phys. B, 2022, 31(8): 083103.
[2]	Ultrafast proton transfer dynamics of 2-(2'-hydroxyphenyl)benzoxazole dye in different solvents Simei Sun(孙四梅), Song Zhang(张嵩), Jiao Song(宋娇), Xiaoshan Guo(郭小珊), Chao Jiang(江超), Jingyu Sun(孙静俞), and Saiyu Wang(王赛玉). Chin. Phys. B, 2022, 31(2): 027803.

No Suggested Reading articles found!

Viewed

Full text

Abstract

Cited

Metrics
Related Articles

Theoretical study on twisted intramolecular charge transfer of 1-aminoanthraquinone in different solvents

Cite this article:

Online attention