Novel Photoacid Generators Derived From Allomaltol Containing Terarylenes With 2‐Aminooxazole Fragment

ABSTRACT In this work, we report a new series of efficient neutral photoacid generators (PAGs) based on terarylenes with 2‐aminooxazole bridge fragment. These compounds are readily obtained through a straightforward two‐step approach starting from allomaltol. Wherein, the presence of a hydroxyl group of allomaltol in the terarylene framework enables facile modification with the residues of various acids. It was shown that upon UV‐irradiation such acylated products undergo 6π‐electrocyclization, giving rise to novel polycyclic aromatic compounds with simultaneous release of the corresponding acids. The regiospecificity of investigated process was confirmed by 1 H NMR monitoring. UV–vis absorption and fluorescence studies revealed a strong emission of the acylated precursors and a pronounced decrease in fluorescence upon photoconversion. The developed photoacid generators combine thermal stability, simple preparation procedure with a minimum number of synthetic stages, and effective acid release, which makes them promising for practical applications.

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Publication Details

Journal
Journal of Heterocyclic Chemistry
Published
2025-12-30
DOI
https://doi.org/10.1002/jhet.70157
Primary Topic
Photochromic and Fluorescence Chemistry
Type
article
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article

Novel Photoacid Generators Derived From Allomaltol Containing Terarylenes With 2‐Aminooxazole Fragment

Constantine V. Milyutin, Andrey N. Komogortsev, Alexander V. Migulin
Journal of Heterocyclic Chemistry
Photochromic and Fluorescence Chemistry
article

Novel Photoacid Generators Derived From Allomaltol Containing Terarylenes With 2‐Aminooxazole Fragment

Constantine V. Milyutin, Andrey N. Komogortsev, Alexander V. Migulin
article en

Abstract

ABSTRACT In this work, we report a new series of efficient neutral photoacid generators (PAGs) based on terarylenes with 2‐aminooxazole bridge fragment. These compounds are readily obtained through a straightforward two‐step approach starting from allomaltol. Wherein, the presence of a hydroxyl group of allomaltol in the terarylene framework enables facile modification with the residues of various acids. It was shown that upon UV‐irradiation such acylated products undergo 6π‐electrocyclization, giving rise to novel polycyclic aromatic compounds with simultaneous release of the corresponding acids. The regiospecificity of investigated process was confirmed by 1 H NMR monitoring. UV–vis absorption and fluorescence studies revealed a strong emission of the acylated precursors and a pronounced decrease in fluorescence upon photoconversion. The developed photoacid generators combine thermal stability, simple preparation procedure with a minimum number of synthetic stages, and effective acid release, which makes them promising for practical applications.

Journal of Heterocyclic Chemistry
N.D. Zelinsky Institute of Organic Chemistry (RU)
Openalex Percentile: Top 47%
Photochromic and Fluorescence Chemistry
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Novel Photoacid Generators Derived From Allomaltol Containing Terarylenes With 2‐Aminooxazole Fragment — Constantine V. Milyutin, Andrey N. Komogortsev, et al. · Journal of Heterocyclic Chemistry (2025) | TGRS Research Map | TGRS