Publication: Novel dihydro-1,3,2h-benzoxazine derived from furfurylamine: Crystal structure, hirshfeld surface analysis, photophysical property, and computational study
Issued Date
2021-05-01
Resource Type
ISSN
20734352
Other identifier(s)
2-s2.0-85107219275
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Crystals. Vol.11, No.5 (2021)
Suggested Citation
Worawat Wattanathana, Yuranan Hanlumyuang, Suttipong Wannapaiboon, Kantapat Chansaenpak, Piyanut Pinyou, Tanin Nanok, Pongsakorn Kanjanaboos Novel dihydro-1,3,2h-benzoxazine derived from furfurylamine: Crystal structure, hirshfeld surface analysis, photophysical property, and computational study. Crystals. Vol.11, No.5 (2021). doi:10.3390/cryst11050568 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/76535
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Novel dihydro-1,3,2h-benzoxazine derived from furfurylamine: Crystal structure, hirshfeld surface analysis, photophysical property, and computational study
Abstract
Dihydro-1,3,2H-benzoxazines (or benzoxazine monomers) are a class of compounds that have been widely utilized in many areas such as the production of the functional polymers and optoelectronic materials. The structure variety of the benzoxazines plays a vital role in their desired properties. The effort of synthesizing functionalized benzoxazines from bioresources is of interest for sustainable development. Herein, we report the synthesis of the novel benzoxazine monomer referred to as 3-(furan-2-ylmethyl)-6-methyl-3,4-dihydro-2H-benzo[e][1,3]oxazine or benzoxazine (I) from a one-pot Mannich reaction using p-cresol, paraformaldehyde, and furfurylamine (a bio-derived amine). An X-ray crystallographic study was performed at low temperature (100 K) to obtain the structural characteristics of the benzoxazine (I). The result reveals that the oxazine ring adopts a half chair conformation to locate all the members of the benzoxazine ring as planar as possible by employing the expansion of the bond angles within the ring. Apart from the structural parameters, the intermolecular interactions were also examined. It was found that the significant interactions within the crystal are C–H···N, C–H···O, and the C–H···π interactions. The C–H···N interactions link the benzoxazine (I) molecules into an infinite molecular chain, propagating along the [100] direction. Hirshfeld surfaces and their corresponding fingerprint plots were comprehensively analyzed to confirm and quantify the significance of these interactions. Moreover, the photophysical properties of the benzoxazine (I) were investigated in solvents with various polarities. The corresponding relations between the structural features, frontier molecular orbitals, and absorption-and-emission characteristics were proposed and explained according to the DFT and TD-DFT calculations.