ICCAS OpenIR
7-trifluoromethylquinoline-functionalized luminescent photochromic spiropyran with the stable merocyanine species both in solution and in the solid state
Guo, XF; Zhou, YC; Zhang, DQ; Bing, Y; Liu, ZL; Liu, CM; Lu, ZL; Huang, YH; Zhu, DB
2004-12-10
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume69Issue:25Pages:8924-8931
AbstractA new spiropyran (SP2) with the stable merocyanine form (MC2) both in solution and in the solid state at room temperature was designed and synthesized. The stability of MC2 is believed to be due to the electron-withdrawing effect of both the quinoline and the trifluoromethyl groups. H-1 NMR spectra indicate that the ratio of the open form vs the closed form of SP2 is dependent on the polarity of solvents. Single crystals composed of only the open form (MC2) were successfully obtained. X-ray structural analysis indicates that except trifluoromethyl and two methyl groups MC2 is completely planar with an s-trans,s-cis conformation. It should be noted that this is the first report of the X-ray crystal structure of the pure open form of spiropyran. MC2 can be slowly transformed into SP2 at -30degreesC or lower temperature, and the process is accelerated by visible light irradiation. This special photochromic behavior can be explained by the calculated thermodynamic data. The spectral properties of SP2/MC2 in the presence of different metal ions are also studied, and the results show the potential application of SP2/MC2 in sensing metal ions.
DOI10.1021/jo0487799
Indexed BySCI ; IC
Language英语
WOS IDWOS:000225550300045
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:36[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/82318
Collection中国科学院化学研究所
Corresponding AuthorZhang, DQ
Affiliation1.Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China
2.Chinese Acad Sci, Grad Sch, Beijing 100080, Peoples R China
3.Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China
Recommended Citation
GB/T 7714
Guo, XF,Zhou, YC,Zhang, DQ,et al. 7-trifluoromethylquinoline-functionalized luminescent photochromic spiropyran with the stable merocyanine species both in solution and in the solid state[J]. JOURNAL OF ORGANIC CHEMISTRY,2004,69(25):8924-8931.
APA Guo, XF.,Zhou, YC.,Zhang, DQ.,Bing, Y.,Liu, ZL.,...&Zhu, DB.(2004).7-trifluoromethylquinoline-functionalized luminescent photochromic spiropyran with the stable merocyanine species both in solution and in the solid state.JOURNAL OF ORGANIC CHEMISTRY,69(25),8924-8931.
MLA Guo, XF,et al."7-trifluoromethylquinoline-functionalized luminescent photochromic spiropyran with the stable merocyanine species both in solution and in the solid state".JOURNAL OF ORGANIC CHEMISTRY 69.25(2004):8924-8931.
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