Synthesis and Photophysical Properties of Cyclic Homodimer of U-Shaped Dibenzophenazinylene

2025/10/08 by Naohiro Namba, Satoshi Minakata, Youhei Takeda · 1 voice · 1 citation
Chemistry · Materials Science · #Luminescence and Fluorescent Materials #Porphyrin and Phthalocyanine Chemistry #Synthesis and Properties of Aromatic Compounds

paper · doi:10.1021/acs.orglett.5c03358

openalex publication_date 2025/10/08 · openalex created_date 2025/10/10 · openalex updated_date 2026/03/27

Abstract

A new class of cyclic π-extended heteroarylene oligomer─cyclic homodimer of U-shaped dibenzophenazinylene─has been successfully synthesized and characterized. NMR spectroscopy and DFT calculations implicated the unique topologies of the macrocycle. The cyclic dimer displays intense green-to-yellow fluorescence in both solution and the solid state. Remarkably, it shows acid-responsive color changes and a photoluminescence "turn-OFF" response upon protonation. The heteroaromatic macrocycle represents a versatile scaffold for the development of advanced optoelectronic materials and supramolecular host-guest systems.

Citations

• Synthesis of Solubility‐Enhanced 6,8‐Diarylated Dibromodibenzo[ a,j ]Phenazines via Pd‐Catalyzed C─H Arylation and Skeletal Rearrangement

Cited by

• Highly soluble cyclic dibenzophenazine heterodimer enabled by a tetra-functionalized building block

Discussions

• 🌀New release in Org. Lett. –we’ve made the first cyclic U-shaped dibenzophenazine homodimer, unveiling unexpected photophysics and a new kinked heteroarylene topology. Congrats Naohiro! #PiSky doi.o [bsky, 5 points, 0 comments]

Related

• Highly soluble cyclic dibenzophenazine heterodimer enabled by a tetra-functionalized building block
• Dual‐State Photophysical Modulation via Bifurcated Hydrogen Bonding in a U‐Shaped Dipyridophenazine‐Cored Donor‐π‐Acceptor‐π‐Donor Fluorophore
• Dual-State Photophysical Modulation via Bifurcated Hydrogen Bonding in a U-Shaped Dipyridophenazine-Cored Donor–π–Acceptor–π–Donor Fluorophore
• Tetrabenzo[a,c]phenazine Backbone for Highly Efficient Orange–Red Thermally Activated Delayed Fluorescence with Completely Horizontal Molecular Orientation
• Modulating Bond Order and Aromaticity in Dual‐BN‐Bonded Dihydrophenazine for Multi‐Stimuli Responsiveness