Novel pyrazolyazoindole derivatives as photoswitches: design, synthesis, and photoswitching behavior research combined with theoretical methods

Following the progress on mono-heteroaryl azo switches (Het-N = N-Ph), a few bis-heteroaryl azo switches (Het-N=N-Het) have been studied recently, whereas the nonsymmetric bis-heteroaryl ones (Het 1 -N=N-Het 2 ) that can combine the respective merits of each heterocycle, have received little attention. Here we report thiazolylazopyrazoles as nonsymmetric bis-heteroaryl azo switches that combine the visible-light switching character of the thiazole ring and the ease of osubstitution of the pyrazole ring. Thiazolylazopyrazoles can achieve (near-)quantitative visible-light isomerization in both directions and long Z-isomer thermal halflives of several days. In contrast to the drastically destabilizing effect of o-methylation, o-carbonylation of the pyrazole ring can remarkably stabilize Z isomers by inducing attractive intramolecular interactions (dispersion, CÀ H•••N bond, and lone-pair•••π interaction). Our work highlights the importance of the rational combination of two heterocycles and suitable structural substitution in developing bis-heteroaryl azo switches.

show abstract

Thiazolylazopyrazoles as Nonsymmetric Bis‐Heteroaryl Azo Switches: High‐Yield Visible‐Light Photoisomerization and Increased Z‐Isomer Stability by o‐Carbonylation

Dang

Dong

Zhang

et al. 2023

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Thiazolylazopyrazoles as Nonsymmetric Bis‐Heteroaryl Azo Switches: High‐Yield Visible‐Light Photoisomerization and Increased Z‐Isomer Stability by o‐Carbonylation

et al. 2023

View full text Add to dashboard Cite

Following the progress on mono‐heteroaryl azo switches (Het‐N=N‐Ph), a few bis‐heteroaryl azo switches (Het‐N=N‐Het) have been studied recently, whereas the nonsymmetric bis‐heteroaryl ones (Het1‐N=N‐Het2) that can combine the respective merits of each heterocycle, have received little attention. Here we report thiazolylazopyrazoles as nonsymmetric bis‐heteroaryl azo switches that combine the visible‐light switching character of the thiazole ring and the ease of o‐substitution of the pyrazole ring. Thiazolylazopyrazoles can achieve (near‐)quantitative visible‐light isomerization in both directions and long Z‐isomer thermal half‐lives of several days. In contrast to the drastically destabilizing effect of o‐methylation, o‐carbonylation of the pyrazole ring can remarkably stabilize Z isomers by inducing attractive intramolecular interactions (dispersion, C−H⋅⋅⋅N bond, and lone‐pair⋅⋅⋅π interaction). Our work highlights the importance of the rational combination of two heterocycles and suitable structural substitution in developing bis‐heteroaryl azo switches.

show abstract

3-Pyridylazoindole derivatives as photoswitches: Synthesis, photoswitching behavior research, and applied to “on–off” fluorescence sensor for Cu2+ combined with theoretical calculations

Jing

et al. 2023

Journal of Photochemistry and Photobiology A: Chemistry

View full text Add to dashboard Cite

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Novel pyrazolyazoindole derivatives as photoswitches: design, synthesis, and photoswitching behavior research combined with theoretical methods

Abstract: In order to exploit novel light−driven molecular switches, A series of pyrazolyazoindole photoswitches were designed and synthesized by modifying the nitrogen atoms of indole, three typical title compounds were characterized...

Cited by 6 publications

References 41 publications

Thiazolylazopyrazoles as Nonsymmetric Bis‐Heteroaryl Azo Switches: High‐Yield Visible‐Light Photoisomerization and Increased Z‐Isomer Stability by o‐Carbonylation

Thiazolylazopyrazoles as Nonsymmetric Bis‐Heteroaryl Azo Switches: High‐Yield Visible‐Light Photoisomerization and Increased Z‐Isomer Stability by o‐Carbonylation

Thiazolylazopyrazoles as Nonsymmetric Bis‐Heteroaryl Azo Switches: High‐Yield Visible‐Light Photoisomerization and Increased Z‐Isomer Stability by o‐Carbonylation

3-Pyridylazoindole derivatives as photoswitches: Synthesis, photoswitching behavior research, and applied to “on–off” fluorescence sensor for Cu2+ combined with theoretical calculations

Contact Info

Product

Resources

About