The synthesis and reaction network of 2-styryl-1-benzopyrylium salts: An unexploited class of potential colorants

被引:31
作者
Gomes, Raquel [1 ]
Diniz, Ana M. [1 ]
Jesus, Alexandre [1 ]
Parola, A. Jorge [1 ]
Pina, Fernando [1 ]
机构
[1] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, REQUIMTE, P-2829516 Caparica, Portugal
关键词
Flavylium; 2-Phenyl-1-benzopyrylium; 2-Styryl-1-benzopyrylium; Food colorants; Photochromism; STRUCTURAL TRANSFORMATIONS; AQUEOUS-SOLUTIONS; FLAVYLIUM; PHOTOCHROMISM; HYDRATION; SYSTEMS; KETONES;
D O I
10.1016/j.dyepig.2008.09.007
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The syntheses, thermodynamic and kinetic properties of a series of 2-styryl-1-benzopyrylium compounds are reported. This family of compounds was found to follow the same pH- and light-dependent network of chemical reactions previously described for flavylium (2-phenyl-1-benzopyrylim) compounds. However, 2-styryl-1-benzopyrylium compounds exhibit absorption spectra substantially red shifted when compared with flavylium analogues (up to 90 nm). In particular, a photochromic system switching from yellow to light blue based on derivatives of natural anthocyanins is for the first time documented. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:69 / 79
页数:11
相关论文
共 29 条
  • [11] Jurd L, 1967, Us Patent, Patent No. [3(301):683, 3301683]
  • [12] Katritzky AR, 1998, EUR J ORG CHEM, V1998, P2623
  • [13] Kuster F.W., 1982, Tabelle per le Analisi Chimiche e Chimico Fisiche, V12th, P157
  • [14] Markakis P., 1982, ANTHOCYANINS FOOD CO, P163, DOI DOI 10.1016/B978-0-12-472550-8.50010-X
  • [15] HYDRATION OF THE FLAVYLIUM ION
    MCCLELLAND, RA
    GEDGE, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) : 5838 - 5848
  • [16] HYDRATION OF THE FLAVYLIUM ION .2. THE 4'-HYDROXYFLAVYLIUM ION
    MCCLELLAND, RA
    MCGALL, GH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) : 3730 - 3736
  • [17] Multistate properties of 7-(N,N-diethylamino)-4′-hydroxyflavylium.: An example of an unidirectional reaction cycle driven by pH
    Moncada, MC
    Fernández, D
    Lima, JC
    Parola, AJ
    Lodeiro, C
    Folgosa, F
    Melo, MJ
    Pina, F
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (19) : 2802 - 2808
  • [18] Pina F, 1998, CHEM-EUR J, V4, P2001, DOI 10.1002/(SICI)1521-3765(19981002)4:10<2001::AID-CHEM2001>3.0.CO
  • [19] 2-P
  • [20] Thermal and photochemical properties of 4′,7-dihydroxyflavylium in water-ionic liquid biphasic systems:: A write-read-erase molecular switch
    Pina, F
    Lima, JC
    Parola, AJ
    Afonso, CAM
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1525 - 1527