Crystallographic, thermal, and solid-state photoluminescent investigations of a di-benzoate ester modified benzoxazine dimer derivative
Issued Date
2023-01-01
Resource Type
ISSN
10400400
eISSN
15729001
Scopus ID
2-s2.0-85179680532
Journal Title
Structural Chemistry
Rights Holder(s)
SCOPUS
Bibliographic Citation
Structural Chemistry (2023)
Suggested Citation
Suetrong N., Kanjanaboos P., Yaemphutchong S., Suesuwan A., Chansaenpak K., Wannapaiboon S., Kalnaowakul P., Chuanopparat N., Hanlumyuang Y., Wattanathana W. Crystallographic, thermal, and solid-state photoluminescent investigations of a di-benzoate ester modified benzoxazine dimer derivative. Structural Chemistry (2023). doi:10.1007/s11224-023-02263-4 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/95537
Title
Crystallographic, thermal, and solid-state photoluminescent investigations of a di-benzoate ester modified benzoxazine dimer derivative
Corresponding Author(s)
Other Contributor(s)
Abstract
Benzoxazine dimers are a group of compounds with a variety of properties, such as anticancer properties and good chelating behaviors. The modification of the benzoxazine dimers can be carried out on the OH groups as well as the benzene moiety. There are several works reported on the property adjustment involving the use of different substituent groups on the benzene ring. Only a few works described the properties and crystallographic studies of the OH-modified benzoxazine dimer. The repulsion forces between two bulky benzoyl groups push them to be more distant compared to the unmodified benzoxazine dimer. According to the crystallographic information, the C—H···O, C—H···π, and π···π interactions hold neighbor molecules together, which consequently stabilize the crystal structure. Thermal analyses (TGA and DSC) reveal that the synthesized benzoated benzoxazine dimer is stable up to 175 °C. Hirshfeld surface analysis confirmed the presence of the C—H···O and C—H···π interactions as seen from the high contributions of the following contacts: H···H (60.6%), H···C/C···H (25.1%), and H···O/O···H (12.3%). Moreover, the observed π···π interaction is supported by the shape-index property of the corresponding Hirshfeld surface. For the solid-state photoluminescence of the di-benzoated benzoxazine dimer recorded at the excitation wavelength range from 265 to 320 nm, the emission peak at 490 nm is observed together with another peak or shoulder in the range of 440–480 nm. For all the excitation wavelengths studied, the di-benzoated dimer emits the fluorescence in the blue color shades (CIE coordinate of x at 0.137–0.142 and y at 0.200–0.262). The photoluminescence property is found to originate by the benzoate modification of the benzoxazine dimer.