Citation: FAN Cong-Bin, DUAN Fang, PU Shou-Zhi. Crystal Structure and High Contrast Color-/fluorescent-switching Properties of 1-[2-Methyl-5-(4-chlorophenyl)-3-thienyl]-2-(2-methoxylphenyl)hexafluorocyclopentene[J]. Chinese Journal of Structural Chemistry, ;2015, 34(11): 1675-1681. doi: 10.14102/j.cnki.0254-5861.2011-0737 shu

Crystal Structure and High Contrast Color-/fluorescent-switching Properties of 1-[2-Methyl-5-(4-chlorophenyl)-3-thienyl]-2-(2-methoxylphenyl)hexafluorocyclopentene

1.
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, China

Received Date: 26 March 2015
Available Online: 9 June 2015
Fund Project: Supported by the National Natural Science Foundation of China (51373072, 21363009) (51373072, 21363009) the Project of Natural Science Foundation of Jiangxi Province (20142BAB203005) (20142BAB203005)the Program for the Top Young Innovative Talents in University (2013QNBJRC002) (2013QNBJRC002)

A new photochromic diarylethene, [1-(2-methyl-5-(4-chlorophenyl)-3-thienyl-2-(2-methoxylphenyl)]perfluorocyclopentene (1o, C₂₃H₁₅ClF₆OS) was synthesized and its structure was determined by single-crystal X-ray diffraction analysis. The crystal belongs to the triclinic system, space group P1 with a=9.421(1), b=10.4664(1), c=11.2988(2), α=88.014(1), β=76.976(1), γ=82.319(1)°, Z=2, V=1075.7(2) Å³, D_c=1.509 mg/m³, μ=0.339 mm^-1, F(000)=496, the final R=0.0353 and wR=0.0922 for 3303 observed reflections (I>2σ(I)). Further study demonstrated this compound underwent reversible photochromism with high contrast color-switching between colorless and blue in hexane. Upon UV/Vis irradiation, the fluorescence quenching efficiency can be attached to ca. 98% and recover to the initial state which exhibits high contrast fluorescent-switching between "on" and "off" states.
- single-crystal,
- X-ray,
- diarylethene,
- photochromism,
- fluorescent-switching
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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [12]
  Hang Meng , Bicheng Zhu , Ruolun Sun , Zixuan Liu , Shaowen Cao , Kan Zhang , Jiaguo Yu , Jingsan Xu . Dynamic photoluminescence switching of carbon nitride thin films for anticounterfeiting and encryption. Chinese Journal of Structural Chemistry, 2024, 43(10): 100410-100410. doi: 10.1016/j.cjsc.2024.100410
13. [13]
  Zhaohong Chen , Mengzhen Li , Jinfei Lan , Shengqian Hu , Xiaogang Chen . Organic ferroelastic enantiomers with high T_c and large dielectric switching ratio triggered by order-disorder and displacive phase transition. Chinese Chemical Letters, 2024, 35(10): 109548-. doi: 10.1016/j.cclet.2024.109548
14. [14]
  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
15. [15]
  Xuan Zhu , Lin Zhou , Xiao-Yun Huang , Yan-Ling Luo , Xin Deng , Xin Yan , Yan-Juan Wang , Yan Qin , Yuan-Yuan Tang . (Benzimidazolium)2GeI4: A layered two-dimensional perovskite with dielectric switching and broadband near-infrared photoluminescence. Chinese Journal of Structural Chemistry, 2024, 43(6): 100272-100272. doi: 10.1016/j.cjsc.2024.100272
16. [16]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
17. [17]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(587)
HTML views(2)

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

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return