Citation: Feng JIN, Qi-Juan XIONG, Zhuo-Ni LIU, Ya-Ting XIAO, Fang YANG, Ting-Ting CHENG, Lin ZHANG, Dong-Liang TAO, Rong-Bao LIAO, Yong LIU. Structure, Calculation, Optical Properties and Bioimaging of an Organic Fluorescence Compound[J]. Chinese Journal of Structural Chemistry, ;2021, 40(10): 1291-1297. doi: 10.14102/j.cnki.0254–5861.2011–3176 shu

Structure, Calculation, Optical Properties and Bioimaging of an Organic Fluorescence Compound

a.
College of Chemical and Material Engineering, Fuyang Normal University, Fuyang 236037, China
b.
College of Biological and Food Engineering, Fuyang Normal University, Fuyang 236037, China

Corresponding author: Feng JIN, jflyw@163.com Rong-Bao LIAO, liaorongbao1980@ailiyun.com Yong LIU, liuyong@fync.edu.cn
Received Date: 11 March 2021
Accepted Date: 21 April 2021

Fund Project: the Major Project of Natural Science Research in Universities of Anhui Province KJ2020A0533the Major Project of Natural Science Research in Universities of Anhui Province KJ2020A0525Natural Science Foundation of Anhui Province 1508085MB21National Students Research Training Program 201910371016National Students Research Training Program 201910371004National Students Research Training Program S202010371055Research Innovation Team of Fuyang Normal University kytd201710

Figures(7)

A π-conjugated optical functional organic compound comprising an electron donor (D) and acceptor (A) was synthesized. The crystal structure was determined through single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P2₁ with a = 9.6610(5), b = 8.9093(4), c = 26.303(1) Å, β = 96.262(4)°, V = 2250.5(2) Å³, Z = 4, D_c = 1.220 Mg/m³, F(000) = 872, Μ_r = 413.50, μ = 0.072 mm^-1, the final R = 0.0569 and wR = 0.1700 for 8976 observed reflections with I > 2σ(I). Optical properties were studied in detail through theoretical calculation and experimental study. The result reveals that the compound exhibits excellent fluorescence performance and it can be compatible in the cytoplasm of NIH/3T3 cells, showing potential in fluorescence microscopy bioimaging.
- crystal structure,
- theoretical calculation,
- organic fluorescence material,
- bioimaging
1. [1]
  Li, L.; Zhang, C. W.; Ge, J.; Qian, L.; Chai, B. H.; Zhu, Q.; Lee, J. S.; Lim, K. L.; Yao, S. Q. A small-molecule probe for selective profiling and imaging of monoamine oxidase B activities in models of Parkinson's disease. Angew. Chem. Int. Ed. 2015, 54, 10821−10825. doi: 10.1002/anie.201504441
2. [2]
  Li, D. D.; Sun, X. S.; Wang, M. M.; Yu, H.; Zhou, H. P.; Wu, J. Y.; Tian, Y. P. Novel colorimetric detection probe for copper(II) ions based on triphenylamine mixed-valence chromophores bearing prodigious two-photon absorption activity. Sens. Actuators B 2015, 220, 1006–1016. doi: 10.1016/j.snb.2015.06.011
3. [3]
  Jin, F.; Xu, D. L.; Zhou, H. P.; Wu, J. Y.; Tian, Y. P. New conjugated organic dyes with various electron donors: one- and two-photon excited fluorescence, and bioimaging. Dyes. Pigm. 2014, 109, 42–53. doi: 10.1016/j.dyepig.2014.04.032
4. [4]
  Chen, S. Y.; Zhao, M.; Su, J.; Zhang, Q.; Tian, X. H.; Li, S. L.; Zhou, H. P.; Wu, J. Y.; Tian, Y. P. Two novel two-photon excited fluorescent pH probes based on the A-π-D-π-A system for intracellular pH mapping. Dyes. Pigm. 2017, 136, 807–816. doi: 10.1016/j.dyepig.2016.09.020
5. [5]
  Xiao, H. B.; Zhang, Y. Z.; Zhang, W.; Li, S. Z.; Xu, R. H. Two novel dyes containing spirobifluorene and triphenylamine: synthesis, one- and two-photon excited fluorescence and applications as probes for silver ions, water and cell imaging. Sens. Actuators B 2016, 233, 469–475. doi: 10.1016/j.snb.2016.04.101
6. [6]
  Jin, F.; Rong, Z. K.; Guo X. J.; Ma, M. Y.; Lv, J. J.; Zhang, L.; Liao, R. B.; Liu, Y.; Tao, D. L.; Tian, Y. P. Novel D-π-A-π-D structural 2, 2΄-bipyridine derivatives with different electron donors: structure, one- and two-photon excited fluorescence and bioimaging. Dyes. Pigm. 2018, 150, 174–180. doi: 10.1016/j.dyepig.2017.12.015
7. [7]
  Kulkarni, R. U.; Vandenberghe, M.; Thunemann, M.; James, F.; Andreassen, O. A.; Djurovic, S.; Devor, A.; Miller, E. W. In vivo two-photon voltage imaging with sulfonated rhodamine dyes. ACS Cent. Sci. 2018, 4, 1371−1378. doi: 10.1021/acscentsci.8b00422
8. [8]
  Kong, L.; Tian, Y. P.; Chen, Q. Y.; Zhang, Q.; Wang, H.; Tan, D. Q.; Xue, Z. M.; Wu, J. Y.; Zhou, H. P.; Yang, J. X. Self-assembly of metal ion induced highly emissive fluorophore-triphenylamine nanostructures: enhanced two-photon action cross-section for bioimaging applications. J. Mater. Chem. C 2015, 3, 570–581. doi: 10.1039/C4TC01605J
9. [9]
  Huang, Y.; Qiu, F.; Shen, L. Y.; Chen, D.; Su, Y.; Yan, D. Y. Combining two-photon-activated fluorescence resonance energy transfer and near-infrared photothermal effect of unimolecular micelles for enhanced photodynamic therapy. ACS Nano. 2016, 10, 10489−10499. doi: 10.1021/acsnano.6b06450
10. [10]
  Kannan, R.; He, G. S.; Yuan, L. X.; Xu, F. M.; Prasad, P. N.; Dombroskie, A. G.; Reinhardt, B. A.; Baur, J. W.; Vaia, R. A.; Tan, L. S. Diphenylaminofluorene-based two-photon-absorbing chromophores with various π-electron acceptors. Chem. Mater. 2001, 13, 1896–1904. doi: 10.1021/cm000747o
11. [11]
  Liu, J.; Zhu, Y. Z.; Tian, X. H.; Li, F.; Wu, J. Y.; Tian, Y. P. Synthesis, crystal structures of a series of novel 2, 2΄: 6΄, 2΄΄-terpyridine derivatives: the influences of substituents on their photophysical properties and intracellular acid organelle targeting. Dyes. Pigm. 2016, 128, 149–157. doi: 10.1016/j.dyepig.2015.10.040
12. [12]
  Ji, L.; Fang, Q.; Yuan, M. S.; Liu, Z. Q.; Shen, Y. X.; Chen, H. F. Switching high two-photon efficiency: from 3, 8, 13-substituted triindole derivatives to their 2, 7, 12-isomers. Org. Lett. 2010, 12, 5192–5195. doi: 10.1021/ol102057t
13. [13]
  Liu, Y. L.; Guo, Y. Q.; Dong, Z. J.; Fu, Y. Conjugate fluorescent compound based on pyrene-imidazole: design, synthesis, crystal structure and fluorescence property. Chin. J. Struct. Chem. 2019, 38, 550–558.
14. [14]
  Zheng, Z.; Zhang, Q.; Yu, Z. P.; Yang, M. D.; Zhou, H. P.; Wu, J. Y.; Tian, Y. P. Four new two-photon absorbing imidazo [4, 5-f] 1, 10-phenanthroline dye derivatives with different dipole moment orientation based on different groups: synthesis, optical characterization and bioimaging. J. Mater. Chem. C 2013, 1, 822–830. doi: 10.1039/C2TC00175F
15. [15]
  Jin, F.; Ye, Z. F.; Liao, R. B.; Qiao, L. Y.; Tao, D. L.; Liu, Y. Crystal structure, one- and two-photon excited fluorescence and bioimaging of a D-π-A structural triphenylamine derivative. Chin. J. Struct. Chem. 2019, 38, 224–232.
16. [16]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A. V.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams-Young, D.; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J. J.; Brothers, E. N.; Kudin, K. N. V.; Staroverov, N.; Keith, T. A.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Martin, R. L.; Morokuma, K.; Farkas, Ö.; Foresman, J. B.; Fox, D. J. Gaussian 16, Revision B. 01. Gaussian, Inc., Wallingford CT 2016.
17. [17]
  Miertuš, S.; Scrocco, E.; Tomasi, J. Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem. Phys. 1981, 55, 117–129. doi: 10.1016/0301-0104(81)85090-2
18. [18]
  Pascual-Ahuir, J. L.; Silla, E.; Tuñón, I. GEPOL: an improved description of molecular-surfaces. 3. A new algorithm for the computation of a solvent-excluding surface. J. Comp. Chem. 1994, 15, 1127–1138. doi: 10.1002/jcc.540151009
19. [19]
  Tomasi, J.; Mennucci, B.; Cammi, R. Quantum mechanical continuum solvation models. Chem. Rev. 2005, 105, 2999–3093. doi: 10.1021/cr9904009
20. [20]
  Lu, T.; Chen, F. W. Multiwfn: a multifunctional wave function analyzer. J. Comput. Chem. 2012, 33, 580–592. doi: 10.1002/jcc.22885
21. [21]
  Jin, F.; Hao, F. Y.; Ma, J. L.; Wu, J. Y.; Tian, Y. P. Synthesis, crystal structure and spectral properties of a novel Co(II) complex containing imidazole derivative. Chin. J. Struct. Chem. 2006, 25, 1303−1308.
22. [22]
  Jin, F.; Lu, T. Q.; Wang, P.; Rong, Z. K.; Wu, X. Q.; Qiao, L. Y.; Liu, Y.; Liao, R. B.; Tao, D. L. Crystal structures, two-photon excited fluorescence and bioimaging of Zn(II) complexes based on D-π-A structural triphenylamine derivative. J. Lumin. 2017, 192, 1127–1132. doi: 10.1016/j.jlumin.2017.08.030
23. [23]
  Sheldrick, G. M. SHELXL-2014/7. Program for the Solution of Crystal Structures. University of Göttingen, Göttingen 2014.
24. [24]
  Jin, F.; Ma, M. Y.; Lv, J. J.; Guo, X. J.; Zha, Q. J.; Sun, L.; Zhang, L.; Liao, R. B. Crystal structure and the third-order nonlinear optical property of a cadmium(II) complex based on a D-π-A structural organic ligand. Chin. J. Struct. Chem. 2019, 38, 1099–1106.
1. [1]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
2. [2]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
3. [3]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
4. [4]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
5. [5]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
6. [6]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
7. [7]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
8. [8]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
9. [9]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
10. [10]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
11. [11]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
12. [12]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
13. [13]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
14. [14]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
15. [15]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
16. [16]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
17. [17]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
18. [18]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
19. [19]
  Shaohua Zhang , Liyao Liu , Yingqiao Ma , Chong-an Di . Advances in theoretical calculations of organic thermoelectric materials. Chinese Chemical Letters, 2024, 35(8): 109749-. doi: 10.1016/j.cclet.2024.109749
20. [20]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(314)
HTML views(3)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142