Palladium Complexes of Carbazole-Based Chalcogenaisophlorins: Synthesis, Structure, and Solid-State NIR Absorption Spectra
Related Experiment Video
Updated: Dec 30, 2025

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Chihiro Maeda1, Kazuto Takaishi1, Tadashi Ema1
1Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Okayama, 700-8530, Japan.
Abstract:
Annulation reactions of the butadiyne-bridged carbazole dimer 1 produced carbazole-based chalcogenaisophlorins 2-4, which were transformed into the corresponding palladium complexes 2Pd-4Pd. The structures were characterized by NMR spectroscopy and X-ray diffraction analysis. Metallation fixed the structures which displayed weak antiaromatic character derived from the 20π isophlorin framework. These complexes showed weak near-infrared (NIR) absorption typical for antiaromatic porphyrinoids in solution. In addition, 2Pd and 3Pd showed relatively strong solid-state NIR absorption. X-ray diffraction analyses of 2Pd and 3Pd revealed trimeric and dimeric stacked layered structures, respectively, and DFT calculations suggest that the solid-state NIR absorption is ascribed to intermolecular charge transfer.
More Related Videos
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
12:07Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Related Concept Videos
Variables Affecting Phosphorescence and Fluorescence
Spectroscopy of Carboxylic Acid Derivatives
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
UV–Vis Spectroscopy: Woodward–Fieser Rules
Crystal Field Theory - Octahedral Complexes
To explain the observed behavior of transition metal complexes (such as colors), a model involving electrostatic interactions between the electrons from the ligands and the electrons in the unhybridized d orbitals of the central metal atom has been developed. This electrostatic model is crystal field theory (CFT). It helps to understand, interpret, and predict the colors, magnetic behavior, and some structures of coordination compounds of transition metals.
CFT focuses on...