Synthesis of UV absorbers based on N‑(2‑aminoaryl)benzotriazole derivatives

Alexander Khlopotinin; Irina Chuvakova; Ivan Tihonov; Zhanna Chirkova; Roman Begunov

doi:10.52957/2782-1900-2026-7-3-113-122

UDC 547.791.8

SYNTHESIS OF UV ABSORBERS BASED ON N‑(2‑AMINOARYL)BENZOTRIAZOLE DERIVATIVES Synthesis of UV absorbers based on N‑(2‑aminoaryl)benzotriazole derivatives

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Published in From Chemistry Towards Technology Step-By-Step · Volume 7, Issue 3, 2026 · Pages 113–122 · Rubric: Scientific articles

DOI: https://doi.org/10.52957/2782-1900-2026-7-3-113-122

Received: 08.06.2026 Accepted: 12.08.2026 Published: 02.10.2026 Language of publication: ENG

Authors

Alexander Khlopotinin

Irina Chuvakova

Ivan Tihonov

Zhanna Chirkova

et al.

Roman Begunov

Alexander Khlopotinin

Academic degree: candidate of chemical sciences

P.G. Demidov Yaroslavl State University Chemical Engineer · Yaroslavl

Irina Chuvakova

Yaroslavl State University Student · Yaroslavl

Ivan Tihonov

Academic degree: candidate of chemical sciences

Yaroslavl State University Associate Professor · Yaroslavl

Zhanna Chirkova

Academic degree: doctor of chemical sciences

Science rang: docent

Yaroslavl State Technical University Professor · Biotehnologiya i farmacevticheskiy inzhiniring · Yaroslavl

Roman Begunov

Academic degree: candidate of chemical sciences

Yaroslavl State University Associate Professor · Yaroslavl

ABSTRACT

Through the aromatic nucleophilic substitution and reduction reactions, we obtain mixtures of 1-(2-NH2-4-CF3-phenyl)-1H- and 2-(2-NH2-4-CF3-phenyl)-2H-benzotriazoles, containing 1- and 2‑substituted isomers in various ratios. The UV absorption intensity of these amino compound mixtures was studied. All mixtures of aminobenzotriazole derivatives had absorption in the ranges of 280–200 nm, 315–280 nm, and 400–315 nm. An increase in the content of the 2‑substituted isomer in the mixture resulted in their higher ability to absorb UVA and UVB radiation. When the 1‑substituted derivative predominated in the mixture, UVC radiation was absorbed more intensely. The most promising mixture was found to be one containing the 1- and 2‑substituted isomers in a ratio of 1 : 0.49. It exhibited continuous and significant absorption over the entire studied UV spectral range. Quantum chemical calculations showed the hypsochromic shift of the absorption maxima in the UV spectrum of the 1‑substituted isomer is due to steric hindrance. It makes the molecule substantially non‑planar and disrupts the conjugation between the benzotriazole and aniline moieties. It increases both the energy gap between the HOMO and LUMO and in the energy of electronic transitions.

KEYWORDS

UV absorbers, N-(2-aminoaryl)benzotriazoles, SNAr reaction, reduction, UV spectra, wavelength range 280–200 nm, 315–280 nm and 400–315 nm, quantum chemical modeling

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Khlopotinin A. I., Chuvakova I. M., Tihonov I. V., Chirkova Z. V., Begunov R. S. Synthesis of UV absorbers based on N‑(2‑aminoaryl)benzotriazole derivatives // From Chemistry Towards Technology Step-By-Step. 2026. no. 3. pp. 113-122. DOI: https://doi.org/10.52957/2782-1900-2026-7-3-113-122. (Date of access 24.10.2026).

MLA

Alexander Khlopotinin, Chuvakova I. M., Tihonov I. V., Chirkova Z. V., Begunov R. S.. "Synthesis of UV absorbers based on N‑(2‑aminoaryl)benzotriazole derivatives." From Chemistry Towards Technology Step-By-Step 7.3 (2026): 113-122. DOI: https://doi.org/10.52957/2782-1900-2026-7-3-113-122.

APA

Khlopotinin A. I., Chuvakova I. M., Tihonov I. V., Chirkova Z. V., Begunov R. S. (2026). Synthesis of UV absorbers based on N‑(2‑aminoaryl)benzotriazole derivatives. From Chemistry Towards Technology Step-By-Step, 7(3), 113-122. https://doi.org/10.52957/2782-1900-2026-7-3-113-122

Chicago

Alexander Khlopotinin, Chuvakova I. M., Tihonov I. V., Chirkova Z. V., Begunov R. S.. "Synthesis of UV absorbers based on N‑(2‑aminoaryl)benzotriazole derivatives." From Chemistry Towards Technology Step-By-Step 7, no. 3 (2026): 113-122. https://doi.org/10.52957/2782-1900-2026-7-3-113-122.

WIKI

{{cite journal | author = Khlopotinin A. I., Chuvakova I. M., Tihonov I. V., Chirkova Z. V., Begunov R. S. | title = Synthesis of UV absorbers based on N‑(2‑aminoaryl)benzotriazole derivatives | journal = From Chemistry Towards Technology Step-By-Step | year = 2026 | volume = 7 | issue = 3 | pages = 113-122 | doi = 10.52957/2782-1900-2026-7-3-113-122 }}

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SYNTHESIS OF UV ABSORBERS BASED ON N‑(2‑AMINOARYL)BENZOTRIAZOLE DERIVATIVES Synthesis of UV absorbers based on N‑(2‑aminoaryl)benzotriazole derivatives

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