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

463 Pages Posted: 23 Oct 2018 Publication Status: Under Review

See all articles by Stefano Crespi

Stefano Crespi

University of Pavia - PhotoGreen Lab

Nadja A. Simeth

University of Regensburg - Institute of Organic Chemistry

Alfredo Bellisario

University of Pavia - Dipartimento di Fisica

Maurizio Fagnoni

University of Pavia - PhotoGreen Lab

Burkhard König

University of Regensburg - Institute of Organic Chemistry

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Abstract

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, in terms of photophysical and (photo)chemical properties, promoting them as ideal scaffolds for a huge variety of applications based on bi-stable light-addressable systems. However, most of the characteristics exhibited by heteroaryl azoswitches were found empirically and only few works focus on their rationalization. Herein we report on a mechanistic study employing phenylazoindoles as a model reference, combining spectroscopic experiments with a 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 and, consequently, crucial for their future development.

Suggested Citation

Crespi, Stefano and Simeth, Nadja A. and Bellisario, Alfredo and Fagnoni, Maurizio and König, Burkhard, Unraveling the Thermal Isomerization Mechanisms of Heteroaryl Azoswitches: Phenylazoindoles as Case Study (October 23, 2018). Available at SSRN: https://ssrn.com/abstract=3271628 or http://dx.doi.org/10.2139/ssrn.3271628
This version of the paper has not been formally peer reviewed.

Stefano Crespi

University of Pavia - PhotoGreen Lab

Corso Strada Nuova, 65
27100 Pavia, 27100
Italy

Nadja A. Simeth

University of Regensburg - Institute of Organic Chemistry

93040 Regensburg
D-93040 Regensburg, 93053
Germany

Alfredo Bellisario

University of Pavia - Dipartimento di Fisica

Pavia
Italy

Maurizio Fagnoni

University of Pavia - PhotoGreen Lab ( email )

Corso Strada Nuova, 65
27100 Pavia, 27100
Italy

Burkhard König (Contact Author)

University of Regensburg - Institute of Organic Chemistry ( email )

93040 Regensburg
D-93040 Regensburg, 93053
Germany

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