Synthesis, photophysical properties, and monitoring photoisomerization of carbazole-based<i> N</i>-acylhydrazone compound using ion mobility mass spectrometry


Keskin E., Ozturk S., ATAKAY M., UZGÖREN BARAN A., SALİH B.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, vol.470, 2026 (SCI-Expanded, Scopus) identifier

Abstract

The field of organic chemistry has long been fascinated by the versatility and potential of N-acyl hydrazone compounds. These compounds have attracted significant attention due to their remarkable pharmacological properties, diverse synthetic applications, and attractive structural features. Literature has shown that these structures are known to have photo-reactive properties and could cause reversible E/Z isomerization reactions under UV irradiation and heating conditions. We focused on investigating the structure of the acylhydrazone, which has an ortho-pyridine ring derivative. Compound PyAc (Pyridine N-Acylhydrazone) was synthesized for the first time, and reversible E/Z isomerization explanation via hydrogen bond through the pyridine ring has been presented in the literature. 1H NMR and Attached Proton Test (APT) NMR observed the behavior of compound PyAc under these conditions. Structural alterations of the PyAc towards UV light application were investigated by trapped ion mobility spectrometry-time-of-flight-mass spectrometry (TIMS-TOF-MS) technique in the positive ion mode. Ion mobility-mass spectrometry (IM-MS) analyses provided structural information on the monomeric and dimeric forms of PyAc with singly charged cations such as Li+, Na+, K+, and Ag+. These analyses demonstrated that the UV light application to PyAc induces structural alterations. The interactions of different metal cations with PyAc were provided to distinguish between bare and UV-irradiated PyAc in the gas phase.