Reversible Photoluminescence of an H‑Bonded Organic Framework Based on Macrocyclic Triazine in Solvation and Desolvation

Reaction of tert-butyl 3,5-diaminobenzoate with cyanuric chloride gave triazine-based macrocycle 1 in 44.3% yield, which was characterized by 1H and 13C NMR spectroscopy, mass spectrometry, and elemental analysis. A thermally stable HOF-1 from macrocycle 1 was crystallized from hexane–THF, and its p...

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Bibliographic Details
Published in:Crystal growth & design 2020-10, Vol.20 (10), p.6421-6429
Main Authors: Lu, Yao-Chih, Lee, Cheng-Hua, Kuo, Han-Hsuan, Chiang, Hua-Chan, Yao, Cheng-Ter, Sung, Hui-Ling, Lee, Gene-Hsiang, Lai, Long-Li
Format: Article
Language:English
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Summary:Reaction of tert-butyl 3,5-diaminobenzoate with cyanuric chloride gave triazine-based macrocycle 1 in 44.3% yield, which was characterized by 1H and 13C NMR spectroscopy, mass spectrometry, and elemental analysis. A thermally stable HOF-1 from macrocycle 1 was crystallized from hexane–THF, and its porous property was studied. The crystallographic analysis revealed that the void space was maintained by the π–π, H-bond, and C–H−π interactions between the aromatic moieties in a solid state. The framework changes while losing solvents and produces various emission intensities when irradiated. After completely removing the solvents, the void space of HOF 1 was still available for solvation, and surprisingly, the framework almost recovered after adsorbing solvents according to the powder-XRD study.
ISSN:1528-7483
1528-7505
DOI:10.1021/acs.cgd.0c00581