Citation: ZHANG Cong-Cong, ZHU Ling, FAN Cong-Bin, PU Shou-Zhi. Crystal Structure and Photoreactive Properties of 1-(2,5-Dimethyl-3-thienyl)-2-[2-methyl-5-(N-(quinolin-8-yl)-2-carboxamide)-3-thienyl)]perfluorocyclopentene[J]. Chinese Journal of Structural Chemistry, ;2016, 35(3): 413-420. doi: 10.14102/j.cnki.0254-5861.2011-0856
-
The photochromic title compound, C26H18F6N2OS2, contains a 2, 5-dimethylthio-phene ring and a N-formyl aminoquinolinyl thiophene ring on the C=C double bond of the cyclopentene ring. The dihedral angles between the cyclopentene and attached N-formyl aminoquinolinyl thiophene ring and 2, 5-dimethylthiophene ring are 63.0° and 137.1°, respectively. The dihedral angle between the thiophene ring and the adjacent aminoquinoline ring is 5.7°. The molecule adopts an antiparallel conformation, with a distance between the two photoreactive C atoms of 3.763 Å. In addition, the absorption and fluorescence spectral changes were measured in acetonitile and solid at room temperature, and the result showed that the title compound could undergo photochromic reaction in both states.
-
Keywords:
- single-crystal,
- X-ray,
- diarylethene,
- photochromism
-
-
[1]
(1) Irie, M. Diarylethenes for memories and switches. Chem. Rev. 2000, 100, 1685-1716.
-
[2]
(2) Fan, C. B.; Cui, S. Q.; Liu, G. Synthesis and crystal structure of 1-(2-methyl-5-formyl-3-thienyl)-2-(2-methoxylphenyl) perfluorocyclopentene. Chin. J. Struct. Chem. 2013, 32, 51-56.
-
[3]
(3) Tsujioka, T.; Matsui, N. Electrical characterization of photochromic diarylethene films consisting of extraordinarily large crystallites. J. Mater. Chem. C 2014, 2, 3589-3596.
-
[4]
(4) Jin, H. Y.; Tian, J. H.; Wang, S. R.; Tan, T. F.; Xiao, Y.; Li, X. G. Novel photochromic and electrochromic diarylethenes bearing triphenylamine units. RSC Adv. 2014, 4, 16839-16848.
-
[5]
(5) Irie, M.; Fukaminato, T.; Matsuda, K.; Kobatake, S. Photochromism of diarylethene molecules and crystals: memories, switches, and actuators. Chem. Rev. 2014, 114, 12174-12277.
-
[6]
(6) Pu, S. Z.; Ma, L. L.; Liu, G.; Ding, H. C.; Chen, B. A multiple switching diarylethene with a phenyl-linked rhodamine B unit and its application as chemosensor for Cu2+. Dyes Pigm. 2015, 113, 70-77.
-
[7]
(7) Göstl, R.; Senf, A.; Hecht, S. Remote-controlling chemical reactions by light: towards chemistry with high spatio-temporal resolution. Chem. Soc. Rev. 2014, 43, 1982-1996.
-
[8]
(8) Tian, H.; Yang, S. J. Recent progresses on diarylethene based photochromic switches. Chem. Soc. Rev. 2004, 33, 85-97.
-
[9]
(9) Luo, Q. F.; Fan, Q. L.; Huang, W. A survey on the synthesis of photochromic material diarylethenes. Chin. J. Org. Chem. 2007, 27, 175-187.
-
[10]
(10) Genre, C.; Matouzenko, G. S.; Jeanneau, E.; Luneau, D. A spin-crossover iron(II) coordination polymer with the 8-aminoquinoline ligand: synthesis, crystal structure and magnetic properties of [Fe(aqin)2(4, 4'-bpy)](ClO4)2·2EtOH (aqin = 8-aminoquinoline, 4, 4'-bpy = 4, 4'-bipyridyl). New J. Chem. 2006, 30, 1669-1674.
-
[11]
(11) Schmidbaur, H.; Kolb, A.; Bissinger, P. Synthesis and structure of trinuclear and novel tetranuclear gold(I) complexes derived from 8-aminoquinoline. Inorg. Chem. 1992, 31, 4370-4375.
-
[12]
(12) Zhang, Y.; Guo, X. F.; Si, W. X.; Jia, L. H.; Qian, X. H. Ratiometric and water-soluble fluorescent zinc sensor of carboxamidoquinoline with an alkoxyethylamino chain as receptor. Org. Lett. 2008, 10, 473-476.
-
[13]
(13) Huang, J. H.; Xua, Y. F.; Qian, X. H. Rhodamine-based fluorescent off-on sensor for Fe3+ in aqueous solution and in living cells: 8-aminoquinoline receptor and 2:1 binding. Dalton Trans. 2014, 43, 5983-5989.
-
[14]
(14) Sherwood, J. A.; Gachihi, G. S.; Muigai, R. K.; Skillman, D. R.; Mugo, M.; Rashid, J. R.; Schuster, B. G. Phase 2 efficacy trial of an oral 8-aminoquinoline (WR6026) for treatment of visceral leishmaniasis. Clin. Infect. Dis. 1994, 19, 1034-1039.
-
[15]
(15) Irvine, G. J.; Rickard, C. E.; Roper, W. R.; Williamson, A.; Wright, L. J. A base-stabilized terminal borylene complex of osmium derived from reaction between a dichloroboryl complex and 8-aminoquinoline. Angew. Chem. Int. Ed. 2000, 39, 948-950.
-
[16]
(16) Zhu, J. F.; Yuan, H.; Chan, W. H.; Lee, A. W. A fret fluorescent chemosensor spaq for Zn2+ based on a dyad bearing spiropyran and 8-aminoquinoline unit. Tetrahedron Lett. 2010, 51, 3550-3554.
-
[17]
(17) Tang, B.; Yue, T. X.; Wu, J. S.; Dong, Y. M.; Ding, Y.; Wang, H. J. Rapid and sensitive spectrofluorimetric determination of trace amount of Cr(III) with o-vanillin-8-aminoquinoline. Talanta 2004, 64, 955-960.
-
[18]
(18) Pu, S. Z.; Luo, F. S.; Wang, R. J.; Yang, T. S. 1-(2, 5-Dimethyl-3-thienyl)-3, 3, 4, 4, 5, 5-hexafluoro-2-(5-formyl-2-methyl-3-thienyl) cyclopent-1-ene: a new photochromic diarylethene compound. Acta Crystallogr. E 2006, 62, 1194-1196.
-
[19]
(19) Sevez, G.; Pozzo, J. L. Toward multi-addressable molecular systems: efficient synthesis and photochromic performance of unsymmetrical bisthienylethenes. Dyes Pigm. 2011, 89, 246-253.
-
[20]
(20) Woodward, R. B.; Hoffmann, R. The conservation of orbital symmetry. Angew. Chem., Int. Ed. Engl. 1969, 8, 781-853.
-
[21]
(21) Jia, H. J.; Fan, C. B.; Pu, S. Z. Crystal structure and photochromic properties of [1-(2-methyl-5-(4-cyanophenyl)-3-thienyl)-2-(2-methyl-5-phenyl- 3-thienyl)perfluorocyclopentene. Chin. J. Struct. Chem. 2015, 34, 208-214.
-
[22]
(22) Ramamurthy, V.; Venkatesan, K. Photochemical reactions of organic crystals. Chem. Rev. 1987, 87, 433-481.
-
[23]
(23) Yang, T. S.; Liu, Q.; Li, J. C.; Pu, S. Z.; Yang, P. Y.; Li, F. Y. Photoswitchable upconversion nanophosphors for small animal imaging in vivo. RSC Adv. 2014, 4, 15613-15619.
-
[24]
(24) Fan, C. B.; Pu, S. Z.; Liu, G. Effects of solvents on the growth of an asymmetrical photochromic diarylethene crystal. Dyes Pigm. 2015, 113, 61-69.
-
[25]
(25) Irie, M. Photochromism of diarylethene single molecules and single crystals. Photochem. Photobiol. Sci. 2010, 9, 1535-1542.
-
[26]
(26) Tian, H.; Qin, B.; Yao, R. X.; Zhao, X. L.; Yang, S. J. A single photochromic molecular switch with four optical outputs probing four inputs. Adv. Mater. 2003, 15, 2104-2107.
-
[27]
(27) Fukaminato, T.; Sasaki, T.; Kawai, T.; Tamai, N.; Irie, M. Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level. J. Am. Chem. Soc. 2004, 126, 14843-14849.
-
[28]
(28) Tian, H.; Feng, Y. L. Next step of photochromic switches. J. Mater. Chem. 2008, 18, 1617-1622.
-
[29]
(29) Sevez, G.; Gan, J.; Delbaere, S.; Vermeersch, G.; Sanguinet, L.; Levillain, E.; Pozzo, J. L. Photochromic performance of a dithienylethene-indolinooxazolidine hybrid. Photochem. Photobiol. Sci. 2010, 9, 131-135.
-
[30]
(30) Tsivgoulis, G. M.; Lehn, J. M. Photoswitched and functionalized oligothiophenes: synthesis and photochemical and electrochemical properties. Chem. Eur. J. 1996, 2, 1399-1406.
-
[1]
-
-
[1]
Huirong LIU , Hao XU , Dunru ZHU , Junyong ZHANG , Chunhua GONG , Jingli XIE . Syntheses, structures, photochromic and photocatalytic properties of two viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1368-1376. doi: 10.11862/CJIC.20240066
-
[2]
Hongwei Ma , Fang Zhang , Hui Ai , Niu Zhang , Shaochun Peng , Hui Li . Integrated Crystallographic Teaching with X-ray,TEM and STM. University Chemistry, 2024, 39(3): 5-17. doi: 10.3866/PKU.DXHX202308107
-
[3]
Jingqi Ma , Huangjie Lu , Junpu Yang , Liangwei Yang , Jian-Qiang Wang , Xianlong Du , Jian Lin . Rational design and synthesis of a uranyl-organic hybrid for X-ray scintillation. Chinese Journal of Structural Chemistry, 2024, 43(5): 100275-100275. doi: 10.1016/j.cjsc.2024.100275
-
[4]
Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
-
[5]
Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
-
[6]
Hong-Jin Liao , Zhu Zhuo , Qing Li , Yoshihito Shiota , Jonathan P. Hill , Katsuhiko Ariga , Zi-Xiu Lu , Lu-Yao Liu , Zi-Ang Nan , Wei Wang , You-Gui Huang . A new class of crystalline X-ray induced photochromic materials assembled from anion-directed folding of a flexible cation. Chinese Chemical Letters, 2024, 35(8): 109052-. doi: 10.1016/j.cclet.2023.109052
-
[7]
Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
-
[8]
Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
-
[9]
Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
-
[10]
Fengyu Zhang , Yali Liang , Zhangran Ye , Lei Deng , Yunna Guo , Ping Qiu , Peng Jia , Qiaobao Zhang , Liqiang Zhang . Enhanced electrochemical performance of nanoscale single crystal NMC811 modification by coating LiNbO3. Chinese Chemical Letters, 2024, 35(5): 108655-. doi: 10.1016/j.cclet.2023.108655
-
[11]
Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
-
[12]
Jiakun Bai , Junhui Jia , Aisen Li . An elastic organic crystal with piezochromic luminescent behavior. Chinese Journal of Structural Chemistry, 2024, 43(6): 100323-100323. doi: 10.1016/j.cjsc.2024.100323
-
[13]
Peng Meng , Qian-Cheng Luo , Aidan Brock , Xiaodong Wang , Mahboobeh Shahbazi , Aaron Micallef , John McMurtrie , Dongchen Qi , Yan-Zhen Zheng , Jingsan Xu . Molar ratio induced crystal transformation from coordination complex to coordination polymers. Chinese Chemical Letters, 2024, 35(4): 108542-. doi: 10.1016/j.cclet.2023.108542
-
[14]
Jun Lu , Jinrui Yan , Yaohao Guo , Junjie Qiu , Shuangliang Zhao , Bo Bao . Controlling solid form and crystal habit of triphenylmethanol by antisolvent crystallization in a microfluidic device. Chinese Chemical Letters, 2024, 35(4): 108876-. doi: 10.1016/j.cclet.2023.108876
-
[15]
Ce Liang , Qiuhui Sun , Adel Al-Salihy , Mengxin Chen , Ping Xu . Recent advances in crystal phase induced surface-enhanced Raman scattering. Chinese Chemical Letters, 2024, 35(9): 109306-. doi: 10.1016/j.cclet.2023.109306
-
[16]
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
-
[17]
Yukai Tong , Zhijun Wu , Bo Zhou , Min Hu , Anpei Ye . Surface tension of single suspended aerosol microdroplets. Chinese Chemical Letters, 2024, 35(4): 109062-. doi: 10.1016/j.cclet.2023.109062
-
[18]
Kun Tang , Yu-Wu Zhong . Water reduction by an organic single-chromophore photocatalyst. Chinese Journal of Structural Chemistry, 2024, 43(8): 100376-100376. doi: 10.1016/j.cjsc.2024.100376
-
[19]
Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO4−, ReO4−). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
-
[20]
Mianying Huang , Zhiguang Xu , Xiaoming Lin . Mechanistic analysis of Co2VO4/X (X = Ni, C) heterostructures as anode materials of lithium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100309-100309. doi: 10.1016/j.cjsc.2023.100309
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(861)
- HTML views(40)