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Influences of chemical functionalities on crystal structures and electrochemical properties of dihydro-benzoxazine dimer derivatives
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Metadata
Document Title
Influences of chemical functionalities on crystal structures and electrochemical properties of dihydro-benzoxazine dimer derivatives
Author
Suetrong N.,Chansaenpak K.,Impeng S.,Pinyou P.,Blay V.,Blay-Roger R.,Lisnund S.,Kanjanaboos P.,Hanlumyuang Y.,Wannapaiboon S.,Wattanathana W.
Name from Authors Collection
Affiliations
Department of Materials Engineering, Faculty of Engineering, Kasetsart University, Bangkok, 10900, Thailand; National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Khlong Nueng, 12120, Thailand; School of Chemistry, Institute of Science, Suranaree University of Technology, 111 University Avenue, Nakhon Ratchasima, 30000, Thailand; Department of Microbiology and Environmental Toxicology, University of California Santa Cruz, Santa Cruz, CA 95064, United States; Instituto de Ciencia Molecular, Universitat de València, Catedrático José Beltrán 2, Paterna, 46980, Spain; Department of Applied Chemistry, Faculty of Science and Liberal Arts, Rajamangala University of Technology Isan, 744, Suranarai Rd., Nakhon Ratchasima, 30000, Thailand; School of Materials Science and Innovation, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand; Synchrotron Light Research Institute, 111 University Avenue, Nakhon Ratchasima, 30000, Thailand
Type
Article
Source Title
Crystals
ISSN
20734352
Year
2021
Volume
11
Issue
8
Open Access
All Open Access, Gold
Publisher
MDPI AG
DOI
10.3390/cryst11080979
Abstract
Dihydro-1,3,2H-benzoxazine dimer derivatives or dihydro-benzoxazine dimers are a class of compounds typically prepared by ring-opening reactions between dihydro-benzoxazines and phenols. Dihydro-benzoxazine dimers act as chelating agents for several transition and rare-earth cations. To better understand the chelating properties, it is necessary to examine their structural features and electrochemical characteristics thoroughly. However, the electrochemical properties of dihydro-benzoxazine dimers have not been tremendously examined. Herein, eight derivatives of dihydro-benzoxazine dimers possessing different substituents on the benzene ring and the tertiaryamine nitrogen were synthesized as model compounds to investigate their influences on crystal structures and electrochemical properties. The crystal structure of the dihydro-benzoxazine dimer, namely 2,2′-(cyclohexylazanediyl)bis(methylene)bis(4-methoxyphenol) (7), is identified for the first time and further used to compare with the crystal structures of other derivatives reported previously. For all the derivatives, intermolecular O–H···O hydrogen bonds are the significant interactions to hold the crystal packing of (7) and also the other derivatives. Hirshfeld surface analyses confirm the presence of intermolecular O–H···O hydrogen bonds. Redox behavior of the eight dihydro-benzoxazine dimers was studied by cyclic voltammetry. An oxidation peak observed at 0.25–0.47 V corresponds to the oxidation of the phenolic –OH group to the phenoxonium intermediate. The shift in the electrochemical peak positions is due to the different abilities of the substituents to stabilize the phenoxonium cation intermediate. The stabilizing power is ranged in the following order: methoxy > dimethyl > ethyl ≈ methyl, and N-cyclohexyl > N-methyl. Thus, the derivative (7), which contains both the methoxy and N-cyclohexyl groups, has the lowest oxidation potential. Our work elucidates the effect of the substituents on the crystal structures and electrochemical properties of the dihydro-benzoxazine dimers. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
Industrial Classification
Knowledge Taxonomy Level 1
Knowledge Taxonomy Level 2
Knowledge Taxonomy Level 3
License
CC BY
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Author
Publication Source
Scopus