Related Experiment Video
Updated: Jun 18, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Charge-transfer interaction between poly(9-vinylcarbazole) and 3,5-dinitrobenzamido group or 3-nitrobenzamido group
Ying Yu1, Yuan Yao, Liyan Wang
1State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, China.
Abstract:
We studied the charge-transfer (CT) interaction between poly(9-vinylcarbazole) (PVK) and 3,5-dinitrobenzamido (DBA) group or 3-nitrobenzamido (NBA) group. The complexation equilibrium constant of PVK and N-butyl-3,5-dinitrobenzamide was found to be larger than that of PVK and N-butyl-3-nitrobenzamide using UV-vis spectroscopy. The desorption process of PVK from a DBA-modified substrate was studied with single molecule force spectroscopy. A lot of force-extension curves with a plateau were observed, which indicated the existence of trainlike conformation. The average desorption force of a PVK chain from the DBA-modified substrate was 28 pN. For comparison, the desorption process of PVK from an NBA-modified substrate was also studied, and an average desorption force of 18 pN was obtained. The apparent interaction energy of a CT complex was calculated on the basis of the desorption force and the surface density of electron acceptors. The obtained apparent interaction energies were 14 and 8 kJ x mol(-1) for the carbazolyl-DBA complex and carbazolyl-NBA complex, respectively. On the basis of the energy of the frontier molecular orbital of carbazole, 3,5-dinitrobenzamide, and 3-nitrobenzamide, the difference in strength between the interactions was interpreted as the influence of the substituent group on the energy of the frontier molecular orbital.
Related Concept Videos
Diazonium Group Substitution: –OH and –H
Electrophilic Aromatic Substitution: Nitration of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Directing Effect of Substituents: ortho–para-Directing Groups
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

