UV-absorbing benzamide-based dendrimer precursors: synthesis, theoretical calculation, and spectroscopic characterization

The ability to tune the structural properties with respect to size, polarity, and terminal functionalities makes dendrimers a highly attractive class of compounds with potential biological and catalytic applications. In the present study, Janus (J) and Twin (T) benzamide-based branched structures were synthesized from a primary precursor of methyl gallate and then further characterized using spectroscopic and theoretical techniques. The optimized structures of these dendrimer precursors at the B3LYP/6-311G(d) level revealed that the aliphatic chains in the most stable forms are oriented in the least strained arrangement with the (-benzene-O-CH2-) linkage adopting the phenol-like configuration. UV-Vis spectra showed a consistent absorption at nearly 290 nm, suggesting that both molecules absorb within the ultraviolet region and are colorless. Prominent bands, which include the -OH vibrational stretch, the -C = C- stretch, the -C = O stretch, the -C-O in-plane stretch, and the -NH in-plane bending, were assigned and correlated with the structural and electronic aspects of the molecules.

Automated summary

The ability to tune the structural properties of dendrimers with respect to size, polarity, and terminal functionalities makes them highly attractive for potential biological and catalytic applications. The synthesized Janus (J) and Twin (T) benzamide-based branched structures were characterized using spectroscopic and theoretical techniques, revealing the orientation of aliphatic chains and linkage configurations. UV-Vis spectra showed consistent absorption around 290 nm, with assigned prominent bands correlating with the molecules' structural and electronic aspects.