2-氨基苯并噻唑的结构及激发态质子转移动力学

doi:10.7503/cjcu20190112

高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (8): 1679.doi: 10.7503/cjcu20190112

2-氨基苯并噻唑的结构及激发态质子转移动力学

魏馨, 邓要亮, 郑旭明, 赵彦英

浙江理工大学理学院化学系, 杭州 310018

收稿日期:2019-02-22 修回日期:2019-06-23 出版日期:2019-08-10 发布日期:2019-07-12
通讯作者: 赵彦英,女,博士,副教授,主要从事化学反应动力学研究.E-mail:yyzhao@zstu.edu.cn E-mail:yyzhao@zstu.edu.cn
基金资助:
国家自然科学基金（批准号：21473162，21273202）资助.

Ground Structure and Excited State Proton Transfer Reaction of 2-Aminobenzothiazole

WEI Xin, DENG Yaoliang, ZHENG Xuming, ZHAO Yanying

Department of Chemistry, School of Science, Zhejiang Sci-Tech University, Hangzhou 310018, China

Received:2019-02-22 Revised:2019-06-23 Online:2019-08-10 Published:2019-07-12
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21473162, 21273202).

摘要/Abstract

摘要： 通过傅里叶变换红外光谱（FTIR）、傅里叶变换拉曼（FT-Raman）和488 nm拉曼光谱，结合密度泛函理论（DFT）计算研究了2-氨基苯并噻唑（ABT）在晶态和溶剂中的二聚体结构，并解释了质子性溶剂中ABT二聚体与溶剂分子间的氢键作用.电子光谱实验揭示了ABT二聚体的光物理和光化学反应；紫外吸收和荧光发射光谱结果表明，溶剂、激发波长和pH值对ABT二聚件激发态衰变具有调控作用；含时密度泛函理论（TD-DFT）解释了ABT二聚体双荧光现象，提出了高激发态的质子转移机理.

关键词: 2-氨基苯并噻唑, 拉曼光谱, 荧光光谱, 激发态质子转移, 密度泛函理论

Abstract: The ground state structure of 2-aminobenzothiazole(ABT) dimer was studied in solid and different solvents by Fourier transform infrared spectroscopy(FTIR), Raman spectra combined with density functional theory(DFT). Raman spectrum difference between dimer and solvent molecule in different proton solvents was explained by the hydrogen bonding interaction. Electron spectroscopic experiments further revealed the photophysical and photochemical reactions of dimers. Ultraviolet absorption and fluorescence emission spectra showed that the solvent and pH value may control the decay of higher excited states and excited state proton transfer process. Time-dependent density functional theory(TD-DFT) calculations explained the phenomenon of double fluorescence and explored initially the mechanism of double proton transfer in the excited state.

Key words: 2-Aminobenzothiazole, Raman spectroscopy, Fluorescence spectroscopy, Excited state proton transfer(ESPT), Density functional theory(DFT)

中图分类号:

O641

TrendMD:

魏馨, 邓要亮, 郑旭明, 赵彦英. 2-氨基苯并噻唑的结构及激发态质子转移动力学. 高等学校化学学报, 2019, 40(8): 1679.

WEI Xin, DENG Yaoliang, ZHENG Xuming, ZHAO Yanying. Ground Structure and Excited State Proton Transfer Reaction of 2-Aminobenzothiazole. Chem. J. Chinese Universities, 2019, 40(8): 1679.

参考文献 46

[1]	Wang X. Q., Sarris K., Kage K., Zhang D., Brown S., Kolasa T., Surowy C., El Kouhen O., Muchmore S., Brioni J., J. Med. Chem., 2009, 52(1), 170-180
[2]	Michael C., van Zandt, Michael L., Jones D. E., Gunn L. S., Geraci J., Howard J., Diane R., Sawicki J. S., Jorge L., Jacot A., Thomas D., Tatiana P., J. Med. Chem., 2005, 48(9), 3141-3152
[3]	Mortimer C. G., Wells G., Crochard J. P., Stone E. L., Bradshaw T. D., Stevens M. F., Westwell A. D., J. Med. Chem., 2006, 49(1),179-185
[4]	Koltun D. O., Marquart T. A., Shenk K. D., Elzein E., Li Y., Nguyen M., Kerwar S., Zeng D., Chu N., Soohoo D., Bioorg. Med. Chem. Lett., 2004, 14(2), 549-552
[5]	Mylari B. L., Larson E. R., Beyer T. A., Zembrowski W. J., Aldinger C. E., Dee M. F., Siegel T. W., Singleton D. H., Org. Process Res. Dev., 2018, 22, 1663-1671
[6]	Ma J. J., Hu G., Xie L. J., Chen L., Xu B. X., Gong P., Chem. Res. Chinese Universities, 2015, 31(6), 958-963
[7]	Aiello S., Wells G., Stone E. L., Kadri H., Bazzi R., Bell D. R., Stevens M. F., Matthews C. S., Bradshaw T. D., Westwell A. D., J. Med. Chem., 2008, 51(16), 5135-5139
[8]	Hartley D. E. A., The Agrochemicals Handbook, Royal Society of Chemist, London, 1983
[9]	Markley L. D., Geselius T. C., Hamilton C. T., Secor J., Swisher B. A., ACS. Sym. Ser., 1995, 5841, 221-233
[10]	Yao S., Schaferhales K. J., Belfield K. D., Org. Lett., 2008, 9(26), 5645
[11]	Yao H., So M. K., Rao J., Angew. Chem. Int. Ed., 2010, 119(37), 7161-7164
[12]	Komatsu K., Urano Y., Kojima H., Nagano T., J. Am. Chem. Soc., 2007, 129(44), 13447-13454
[13]	Suh J., Yoo S. H., Kim M. G., Jeong K., Ahn J. Y., Kim M. S., Chae P. S., Lee T. Y., Lee J., Angew. Chem. Int. Ed., 2010, 119(37), 7194-7197
[14]	Rodionov V. O., Presolski S. I., Gardinier S., Lim Y. H., Finn M. G., J. Am. Chem. Soc., 2007, 129(42), 12696-12704
[15]	Gholami M., Danaee I., Maddahy M. H., Rashvandavei M., Ind. Eng. Chem. Res., 2013, 52(42), 14875-14889
[16]	Laermer F., Elsaesser T., Kaiser W., Chem. Phys. Lett., 1988, 148(2), 119-124
[17]	Elsaesser T., Kaiser W., Chem. Phys. Lett., 1986, 128(3), 231-237
[18]	Barbara P. F., Brus L. E., Rentzepis P. M., J. Am. Chem. Soc., 1980, 11(46), 5631-5635
[19]	Klöpffer W., Adv. Photochem., 1977, 10, 311-358
[20]	Barbatti M., Aquino A. J., Lischka H., Schriever C., Lochbrunner S., Riedle E., Phys. Chem. Chem. Phys., 2009, 11(9), 1406-1415
[21]	Tseng H. W., Liu J. Q., Chen Y. A., Chao C. M., Liu K. M., Chen C. L., Lin T. C., Hung C. H., Chou Y. L., Lin T. C., J. Phys. Chem. Lett., 2015, 6(8), 1477-1486
[22]	Demchenko A. P., Tang K. C., Chou P. T., Chem. Soc. Rev., 2013, 42(3), 1379-1408
[23]	Hsieh C. C., Jiang C. M., Chou P. T., Acc. Chem. Res., 2010, 43(10), 1364-1374
[24]	Altaylor C., Ashrafe M., Kasha M., P. Natl. Acad. Sci. USA, 1969, 63(2), 253-260
[25]	Moog R. S., Maroncelli M., Cryst. Growth Des., 2014, 14, 500-512
[26]	Chou P. T., Martinez M. L., Cooper W. C., Collins S. T., Mcmorrow D. P., Kasha M., J. Phys. Chem., 1992, 96(13), 5203-5205
[27]	Chou P. T., Tu T. H., Chen Y. T., Chen Y. A., Wei Y. C., Chen Y. H., Chen C. L., Shen J. Y., Chen Y. H., Ho S. Y., Angew. Chem. Int. Ed., 2018, 57(18), 5020-5024
[28]	Katritzky A. R., Rees C. W., Comprehensive Heterocyclic Chemistry, 1984, 3(1), 905-994
[29]	Beckett M. A., J. Chem. Technol. Biot., 2010, 62(3), 317
[30]	Canseco-Márquez L., Gutiérrez-Mayén G., Mendelson Ⅲ J. R., Southwest. Nat., 2003, 48(4), 670-675
[31]	Téllez F., Cruz A., López-Sandoval H., Ramos-García I., Gayosso M., Castillo-Sierra R. N., Paz-Michel B., Nöth H., Flores-Parra A., Contreras R., Eur. J. Org. Chem., 2010, 2004(20), 4203-4214
[32]	Téllez F., Flores-Parra A., Barba-Behrens N., Contreras R., Polyhedron, 2004, 23(16), 2481-2489
[33]	Knizek J., Nöth H., Schlegel A., Eur. J. Inorg. Chem., 2001, 2001(1), 181-187
[34]	Knizek J., Nöth H., J. Organomet. Chem., 2000, 614(24), 168-187
[35]	Zeng Y., Yi R., Int. J. Quantum Chem., 2007, 107(1), 247-258
[36]	Forlani L., Mezzina E., Boga C., Forconi M., Eur. J. Org. Chem., 2010, 2001(14), 2779-2785
[37]	Jones R. O., Gunnarsson O., Rev. Mod. Phys., 1989, 61(3), 689-746
[38]	Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. A. Jr., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Kobayash R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas Ö., Foresman J. B., Ortiz J. V., Cioslowski J., Fox D. J., Gaussian 09, Revision A.01, Gaussian Inc., Wallingford CT, 2009
[39]	Jamróz M. H., Spectrochim. Acta A:Mol. Biomol. Spectrosc., 2013, 114(0), 220-230
[40]	Sarkar J., Chowdhury J., Ghosh M., De R., Talapatra G. B., J. Phys. Chem. B, 2005, 109(26), 12861-12867
[41]	Rai A. K., Singh R., Singh K. N., Singh V. B., Spectrochim. Acta A:Mol. Biomol. Spectrosc., 2006, 63(2), 483-490
[42]	Liu X., Wei X., Zhou H. Q., Meng S., Zhao Y. Y,, Xue J. D., Zheng X. M., J. Phys. Chem. A, 2018, 122(26), 5710-5720
[43]	Meng S., Zhao Y. Y., Xue J. D., Zheng X. M., Spectrochim. Acta A:Mol. Biomol. Spectrosc., 2018, 190, 478-485
[44]	Cheng J. L., Liu D., Li W., Bao L. J., Han K. L., J. Phys. Chem. C, 2015, 119(8), 4242-4251
[45]	Demchenko A. P., Tang K. C., Chou P. T., Chem. Soc. Rev., 2013, 42(3), 1379-1408
[46]	Hsieh C. C., Jiang C. M., Chou P. T., Acc. Chem. Res., 2010, 43(10), 1364-1374

相关文章 15

[1]	何鸿锐, 夏文生, 张庆红, 万惠霖. 羟基氧化铟团簇与二氧化碳和甲烷作用的密度泛函理论研究[J]. 高等学校化学学报, 2022, 43(8): 20220196.
[2]	陈嘉敏, 曲孝章, 齐国华, 徐蔚青, 金永东, 徐抒平. SERS纳米探针对电刺激过程中细胞内产生活性氧的检测[J]. 高等学校化学学报, 2022, 43(6): 20220033.
[3]	黄汉浩, 卢湫阳, 孙明子, 黄勃龙. 石墨炔原子催化剂的崭新道路:基于自验证机器学习方法的筛选策略[J]. 高等学校化学学报, 2022, 43(5): 20220042.
[4]	刘洋, 李旺昌, 张竹霞, 王芳, 杨文静, 郭臻, 崔鹏. Sc₃C₂@C₈₀与[12]CPP纳米环之间非共价相互作用的理论研究[J]. 高等学校化学学报, 2022, 43(11): 20220457.
[5]	程媛媛, 郗碧莹. ·OH自由基引发CH₃SSC $H 3 •$ ⁺自由基裂解反应机理的理论研究[J]. 高等学校化学学报, 2022, 43(10): 20220271.
[6]	周成思, 赵远进, 韩美晨, 杨霞, 刘晨光, 贺爱华. 硅烷类外给电子体对丙烯-丁烯序贯聚合的调控作用[J]. 高等学校化学学报, 2022, 43(10): 20220290.
[7]	王园月, 安梭梭, 郑旭明, 赵彦英. 5-巯基-1, 3, 4-噻二唑-2-硫酮微溶剂团簇的光谱和理论计算研究[J]. 高等学校化学学报, 2022, 43(10): 20220354.
[8]	马丽娟, 高升启, 荣祎斐, 贾建峰, 武海顺. Sc, Ti, V修饰B/N掺杂单缺陷石墨烯的储氢研究[J]. 高等学校化学学报, 2021, 42(9): 2842.
[9]	钟声广, 夏文生, 张庆红, 万惠霖. 电中性团簇MCu₂O_x(M=Cu²⁺, Ce⁴⁺, Zr⁴⁺)上甲烷和二氧化碳直接合成乙酸的理论研究[J]. 高等学校化学学报, 2021, 42(9): 2878.
[10]	黄罗仪, 翁约约, 黄旭慧, 王朝杰. 车前草中黄酮类成分结构和性质的理论研究[J]. 高等学校化学学报, 2021, 42(9): 2752.
[11]	薛谨, 曹小卫, 刘依帆, 王敏. 纸质空心金纳米笼SERS传感器的制备及对非小细胞肺癌患者痰液中miRNAs的快速高灵敏检测[J]. 高等学校化学学报, 2021, 42(8): 2393.
[12]	郑若昕, 张颖, 徐昕. 低标度XYG3双杂化密度泛函的开发与测评[J]. 高等学校化学学报, 2021, 42(7): 2210.
[13]	王建, 张红星. 四配位铂磷光发射体结构与光物理性质关系的理论研究[J]. 高等学校化学学报, 2021, 42(7): 2245.
[14]	胡伟, 刘小峰, 李震宇, 杨金龙. 金刚石纳米线氮空位色心的表面与尺寸效应[J]. 高等学校化学学报, 2021, 42(7): 2178.
[15]	杨一莹, 朱荣秀, 张冬菊, 刘成卜. 金催化炔基苯并二𫫇英环化合成8-羟基异香豆素的理论研究[J]. 高等学校化学学报, 2021, 42(7): 2299.

2-氨基苯并噻唑的结构及激发态质子转移动力学

Ground Structure and Excited State Proton Transfer Reaction of 2-Aminobenzothiazole

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献 46

相关文章 15

编辑推荐

Metrics

本文评价