Controlling excited-state dynamics <i>via</i> protonation of naphthalene-based azo dyes

Martin, Shea M.; Hamburger, Robert C.; Huang, Tao; Fredin, Lisa A.; Young, Elizabeth R.

doi:10.1039/d4cp00242c

Phys. Chem. Chem. Phys.

2024

DOI: 10.1039/d4cp00242c

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Controlling excited-state dynamics via protonation of naphthalene-based azo dyes

Shea M. Martin,

Robert C. Hamburger,

Tao Huang

et al.

Abstract: Azo dyes are a class of photoactive dyes that constitute a major focus of chemical research due to their applications in numerous industrial functions.

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Pinning Down Small Populations of Photoinduced Intermediates Using Transient Absorption Spectroscopy and Time-Dependent Density Functional Theory Difference Spectra to Provide Mechanistic Insight into Controlling Pyridine Azo Dynamics with Protons

Knepp,

Hamburger,

Thongchai

et al. 2024

J. Phys. Chem. Lett.

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In this work, the impact of protonation on the photoisomerization (trans → cis) and reversion (cis → trans) of three pyridine-based azo dyes (PyrN) is investigated by using a combination of transient absorption spectroscopy and time-dependent density functional theory computed difference spectra. The photophysical behaviors of the PyrN dyes are altered by the addition of one or two protons. Protonation of basic pyridine nitrogens results in an ultrafast accelerated reversion mechanism after photoisomerization, while protonation of azo bond nitrogens restricts cis isomer formation entirely. Computed difference spectra provide spectral signatures that are critical for the assignment of low-population long-lived states, providing direct evidence of the accelerated reversion mechanism. Thus, the addition of organic acids can selectively control the photophysics of azo dyes for a wide range of applications, including materials design and pharmaceuticals.

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Pinning Down Small Populations of Photoinduced Intermediates Using Transient Absorption Spectroscopy and Time-Dependent Density Functional Theory Difference Spectra to Provide Mechanistic Insight into Controlling Pyridine Azo Dynamics with Protons

Knepp,

Hamburger,

Thongchai

et al. 2024

J. Phys. Chem. Lett.

View full text Add to dashboard Cite

show abstract

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Controlling excited-state dynamics via protonation of naphthalene-based azo dyes

Abstract: Azo dyes are a class of photoactive dyes that constitute a major focus of chemical research due to their applications in numerous industrial functions.

Cited by 1 publication

References 51 publications

Pinning Down Small Populations of Photoinduced Intermediates Using Transient Absorption Spectroscopy and Time-Dependent Density Functional Theory Difference Spectra to Provide Mechanistic Insight into Controlling Pyridine Azo Dynamics with Protons

Pinning Down Small Populations of Photoinduced Intermediates Using Transient Absorption Spectroscopy and Time-Dependent Density Functional Theory Difference Spectra to Provide Mechanistic Insight into Controlling Pyridine Azo Dynamics with Protons

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