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Updated: Feb 10, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Charge-Transfer Complexes and Fluorescence Modulation in Amide- and Carboxy-Substituted
Julius Green1, Bradley Blake1, Alexander Rash1
1Chemistry Department, State University of New York at Cortland, P.O. Box 2000, Cortland, New York 13045, United States.
Abstract:
A library of amide- and carboxy- functionalized 2-phenyl-1,3,2-benzodiazaborole derivatives was synthesized via microwave-assisted cyclic condensation to explore the effects of pseudoaromaticity on charge-transfer complex (CTC) formation and photophysical behavior. All compounds were characterized by NMR, IR, UV-vis, and fluorescence spectroscopy. While absorbance profiles remained consistent (λmax = 298 - 324 nm), several derivatives exhibited strong bathochromic emission (λem = 363 - 555 nm) and exceptionally large Stokes shifts (Δv > 150 nm), particularly those bearing -OCH3 groups. Red-shifted fluorescence and DFT calculations suggest antiparallel dimeric CTCs stabilized by B-N delocalization. These results highlight amide- and carboxy- 1,3,2-benzodiazaborole frameworks as tunable pseudoaromatic systems with potential applications in optical sensing and functional material design.
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Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

