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

Abstract

Reaction of tert-butyl 3,5-diaminobenzoate with cyanuric chloride gave triazine-based macrocycle 1 in 44.3% yield, which was characterized by 1 H and 13 C 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.

Six Fluorene-Based N-Heterocyclic Carbene Silver(I) Complexes: Structural Study and Recognition for Cu2+

“…In the crystal packing of L 3 H 2 ·(Br) 2 (Figure S1), a two-dimensional network was formed via C–H···Br H-bonds. − In the H-bonds, the hydrogen atoms came from imidazole rings, fluorene, or CH 2 (the data of H-bonds being shown in Table S5). In 1 , two-dimensional layer was formed via C–H···O H-bonds (Figure S2).…”

Recent Advances in Luminescent Hydrogen‐Bonded Organic Frameworks: Structures, Photophysical Properties, Applications

“…reported a novel HOF‐1 based on triazine macrocycle (31). [ 35 ] Special triazine‐based macrocycle formed 2D layered structure by hydrogen bonding and ππ interactions, then formed a 3D network by the weak CHπ interaction between 2D layers. The framework structure was destroyed or recovered when losing or adsorbing solvents respectively, thus producing reversible various emission intensities.…”

A polycatenated hydrogen-bonded organic framework based on embraced macrocyclic building blocks for fluorescence detection of nitrobenzene in water

“…1a). [32][33][34][35][36][37][38][39] Notably, these reported macrocyclic building blocks largely function as symmetric, multi-connective nodes in the HOF structures, whereas their supramolecular features within the three-dimensional assembly remain underexplored.…”