Title
Synthesis, aggregation induced emission and through space conjugation of triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene
Author
Chin-Yang Yu, Yu-Chun Lai
Year
2018
Journal
RSC Advances
Abstract
4-Bromo substituted [2.2]paracyclophane-1,9-diene was synthesized from the corresponding dithia[3.3]paracyclophane in three steps through benzyne Steven rearrangement, oxidation, and a thermal elimination reaction. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene was successfully prepared by the Suzuki–Miyaura cross-coupling reaction of 4-bromo substituted [2.2]paracyclophane-1,9-diene and 4,4,5,5-tetramethyl-2-(4-(1,2,2-triphenylvinyl)phenyl)-1,3,2-dioxaborolane using Pd(OAc)2 as a catalyst, S-Phos as a ligand and K3PO4 as a base. The structures of bromo substituted [2.2] paracyclophane-1,9-diene and triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene were fully characterized by 1H NMR spectroscopy and X-ray crystallography. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene exhibited aggregation-induced emission characteristics when the water fraction was higher than 80% in the THF/water mixtures. 4-Triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene displays much higher fluorescence when the water fraction is 90% compared to that of model compounds due to both through bond and through space conjugation. To the best for our knowledge, we are the first to synthesize triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene with aggregation-induced emission characteristics.
Instrument
FP-8500
Keywords
Fluorescence, Photoluminescence, Aggregation, Quenching, Chemical stability, Quantum yield, Optical properties, Materials