Fabrication of resonance core assisted self-assembling gelators derived from cyclohexanone

• Three novel high-resonance core compounds, BHC-6, BHC-11 and BHC-cho, were synthesized.
• Asymmetric helical constructions were induced via the synthesized chiral BHC-cho.
• The significant aggregation-induced enhanced emission of BHC-11 and the dimer formation of BHC-6 were confirmed.

Three high-resonance core compounds, BHC-6, BHC-11 and BHC-cho, were synthesized. The morphologies of the self-assembled xerogels of the synthesized compounds were studied using SEM and TEM. The molecular interactions and the formation of asymmetric constructions were investigated using temperature-dependent 1H NMR spectroscopy and circular dichroism spectrometry, respectively. The induction of an asymmetric helical structure was further confirmed using TEM. The results show that increasing the resonance length strengthens intermolecular forces, leading to the formation of gels. A chiral environment produces a steric field effect, leading to the formation of asymmetric constructions. The interactions between functional groups were further confirmed using 2D nuclear overhauser effect spectroscopy NMR. The reversible E–Z isomerization and dimer formation of cinnamoyl derivatives were investigated using UV–vis and fluorescence spectrometry, relatively.

As the temperature decreased, the corresponding self-assembly of the molecules led to the formation of gels. As shown in the figure, a significant aggregation-induced enhanced emission (AIEE) of BHC-11 was observed. This was ascribed to the inhibition of vibrational energy loss of the molecules due to the self-assembly.Figure optionsDownload as PowerPoint slide