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Unraveling the Thermal Isomerization Mechanisms of Heteroaryl Azoswitches: Phenylazoindoles as Case Study

Crespi, S., Simeth, N. A., Bellisario, A., Fagnoni, M. & Koenig, B., 7-Mar-2019, In : Journal of Physical Chemistry A. 123, 9, p. 1814-1823 10 p.

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  • Unraveling the Thermal Isomerization Mechanisms of Heteroaryl Azoswitches: Phenylazoindoles as Case Study

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DOI

The research on heteroaromatic azoswitches has been blossoming in recent years due to their astonishingly broad range of properties. Minimal chemical modifications can drastically change the demeanor of these switches, regarding photophysical and (photo)chemical properties, promoting them as ideal scaffolds for a vast variety of applications based on bistable light-addressable systems. However, most of the characteristics exhibited by heteroaryl azoswitches were found empirically, and only a few works focus on their rationalization. Herein we report on a mechanistic study employing phenylazoindoles as a model reference, combining spectroscopic experiments with comprehensive computational analysis. This approach will elucidate the intrinsic correlations between the molecular structure of the switch and its thermal behavior, allowing a more rational design transferable to various heteroaryl azoswitches.

Original languageEnglish
Pages (from-to)1814-1823
Number of pages10
JournalJournal of Physical Chemistry A
Volume123
Issue number9
Publication statusPublished - 7-Mar-2019

    Keywords

  • TO-TRANS ISOMERIZATION, AZO-HYDRAZONE TAUTOMERISM, NITROGEN-HETEROCYCLES, AZOBENZENE, PHOTOSWITCHES, PHOTOISOMERIZATION, ARYLAZOPYRAZOLES

ID: 118615734