Polymorphic and Isomorphic Cocrystals of a N-Salicylidene-3-aminopyridine with Dicarboxylic Acids: Tuning of Solid-State Photo- and Thermochromism

被引:56
作者
Carletta, Andrea [1 ]
Buol, Xavier [1 ]
Leyssens, Tom [2 ]
Champagne, Benoit [1 ]
Wouters, Johan [1 ]
机构
[1] Univ Namur, Dept Chem, Unite Chim Phys Theor & Struct, 61 Rue Bruxelles, B-5000 Namur, Belgium
[2] Catholic Univ Louvain, Inst Condensed Matter & Nanosci, Louvain La Neuve, Belgium
关键词
NONLINEAR-OPTICAL PROPERTIES; SALICYLIDENEANILINE CRYSTALS; PHOTOCHROMIC MATERIALS; INSIGHTS; BEHAVIOR; BASE;
D O I
10.1021/acs.jpcc.6b02734
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The crystal structures and optical properties of (E)-2-methoxy-6-(pyridin-3-yliminomethyl)phenol (1), a N-salicylidene-3-aminopyridine, and its 2:1 dimorphic cocrystals with fumaric acid (2 and 3) and succinic acid (4 and 5) were studied at solid state in order to understand the effects of cocrystallization and molecular packing on their photo- and thermochromic behavior. New criteria for prediction of the chromic properties, based on the rationalization of the intermolecular interaction in the crystal, are also proposed. These results confirm once more the influence of the molecular packing on the chromic properties of solids and extend it to polymorphic and isomorphic cocrystals.
引用
收藏
页码:10001 / 10008
页数:8
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共 30 条
  • [1] The Cambridge Structural Database: a quarter of a million crystal structures and rising
    Allen, FH
    [J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1): : 380 - 388
  • [2] Photochromism of organic compounds in the crystal state
    Amimoto, K
    Kawato, T
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS, 2005, 6 (04) : 207 - 226
  • [3] Solid-state investigation on a new dimorphic substituted N-salicylidene compound: insights into its thermochromic behaviour
    Carletta, A.
    Dubois, J.
    Tilborg, A.
    Wouters, J.
    [J]. CRYSTENGCOMM, 2015, 17 (18) : 3509 - 3518
  • [4] Fluorescent Switches Based on Photochromic Compounds
    Cusido, Janet
    Deniz, Erhan
    Raymo, Francisco M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (13) : 2031 - 2045
  • [5] Solid-state thermochromism studied by variable-temperature diffuse reflectance spectroscopy. A new perspective on the chromism of salicylideneanilines
    Fujiwara, T
    Harada, J
    Ogawa, K
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (13) : 4035 - 4038
  • [6] Photochromism and thermochromism of Schiff bases in the solid state: structural aspects
    Hadjoudis, E
    Mavridis, IM
    [J]. CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) : 579 - 588
  • [7] Supramolecular control of photochromism in a β-cyclodextrin/Schiff base system
    Hadjoudis, Eugene
    Yannakopoulou, Konstantina
    Chatziefthimiou, Spyros D.
    Paulidou, Anastasia
    Mavridis, Irene M.
    [J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2011, 217 (2-3) : 293 - 298
  • [8] Thermo-to-photo-switching of the chromic behavior of salicylideneanilines by inclusion in a porous coordination network
    Haneda, Tsuyoshi
    Kawano, Masaki
    Kojima, Takahiro
    Fujita, Makoto
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (35) : 6643 - 6645
  • [9] X-ray analysis of structural changes in photochromic salicylideneaniline crystals. Solid-state reaction induced by two-photon excitation
    Harada, J
    Uekusa, H
    Ohashi, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) : 5809 - 5810
  • [10] Co-Crystals of a Salicylideneaniline: Photochromism Involving Planar Dihedral Angles
    Hutchins, Kristin M.
    Dutta, Saikat
    Loren, Bradley P.
    MacGillivray, Leonard R.
    [J]. CHEMISTRY OF MATERIALS, 2014, 26 (10) : 3042 - 3044