Photo-dynamic and fluorescent zinc complex based on spiropyran ligand

被引:19
作者
Miguez, Flavio B. [1 ]
Menzonatto, Thiago G. [2 ]
Netto, Jorge Fernandes Z. [1 ]
Silva, Igor M. S. [3 ]
Verano-Braga, Thiago [3 ]
Lopes, Juliana Fedoce [2 ]
De Sousa, Frederico B. [1 ]
机构
[1] Univ Fed Itajuba UNIFEI, LSPS, Inst Fis & Quim, BR-37500903 Itajuba, MG, Brazil
[2] Univ Fed Itajuba UNIFEI, Lab Quim Computac LaQC, Inst Fis & Quim, BR-37500903 Itajuba, MG, Brazil
[3] Univ Fed Minas Gerais UFMG, Dept Fisiol & Biofis, Inst Ciencias Biol, BR-31270901 Belo Horizonte, MG, Brazil
关键词
Zinc; Spiropyran; Coordination complex; Chromism; Computational calculations; PHOTOCHROMISM; DENSITY; NANOPARTICLES; SUBSTITUENT; CALCIUM; BINDING;
D O I
10.1016/j.molstruc.2020.128105
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
Spiropyrans are among a class of organic molecules widely studied as molecular photoswitches. A photochromic and solvatochromic spiropyran-containing Zinc (II) complex (ZnMC) was successfully synthesized and characterized, and its chromic properties were studied. A solid complex was isolated through a precipitation process induced by UV radiation. The binding specificities were studied by FTIRATR spectroscopy and DFT calculations, demonstrating that phenolate and carboxylic acid are the binding sites of merocyanine. Mass spectrometry and computational methods revealed the possibility of two complexes with different geometries, tetrahedral and octahedral; the complex with tetrahedral characteristics proved to be more stable and abundant. ZnMC solvatochromic properties were analyzed, presenting a wide variation in its absorption band in the visible region. We addressed the issue of ZnMC photodegradation in different solvents, and the observed absorbance did not vary after the first cycles for acetonitrile, while, in tetrahydrofuran, the absorbance decayed throughout the 48 cycles of switching between UV and visible light irradiation. (C) 2020 Elsevier B.V. All rights reserved.
引用
收藏
页数:8
相关论文
共 57 条
[1]   Cation-Triggered Drug Release from a Porous Zinc-Adeninate Metal-Organic Framework [J].
An, Jihyun ;
Geib, Steven J. ;
Rosi, Nathaniel L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) :8376-+
[2]  
Anderson J., 2008, 2008 Servant Leadership Roundtable, P1
[3]  
[Anonymous], 2010, Solvents and SolventEffects in Organic Chemistry
[4]  
[Anonymous], 1999, Advanced inorganic chemistry
[5]   Structural and thermochemical properties of a photoresponsive spiropyran and merocyanine pair: Basis set and solvent dependence in density functional predictions [J].
Balasubramanian, Ganesh ;
Schulte, Joachim ;
Mueller-Plathe, Florian ;
Boehm, Michael C. .
CHEMICAL PHYSICS LETTERS, 2012, 554 :60-66
[6]   Probing Metal Ion Complexation of Ligands with Multiple Metal Binding Sites: The Case of Spiropyrans [J].
Baldrighi, Michele ;
Locatelli, Giulia ;
Desper, John ;
Aakeroy, Christer B. ;
Giordani, Silvia .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (39) :13976-13984
[7]   Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines [J].
Balmond, Edward I. ;
Tautges, Brandon K. ;
Faulkner, Andrea L. ;
Or, Victor W. ;
Hodur, Blanka M. ;
Shaw, Jared T. ;
Louie, Angelique Y. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :8744-8758
[8]  
Bamfield P, 2010, CHRONIC PHENOMENA: TECHNOLOGICAL APPLICATIONS OF COLOUR CHEMISTRY, SECOND EDITION, P1
[9]  
Barachevsky V.A., 2017, Review Journal of Chemistry, V7, P334, DOI DOI 10.1134/S2079978017030013
[10]   Bulky guanidinate calcium and zinc complexes as catalysts for the intramolecular hydroamination [J].
Barman, Milan Kr ;
Baishya, Ashim ;
Nembenna, Sharanappa .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2019, 887 :40-47