Substituent Effect on the Structure and Photophysical Properties of Phenylamino- and Pyridylamino-2,1,3-Benzothiadiazoles


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Abstract

4-Bromo-7-phenylamino-2,1,3-benzothiadiazole (1) and 4-bromo-7-(3-pyridylamino)-2,1,3-benzo thiadiazole (2) are synthesized. Their crystal structure and photophysical properties are studied in comparison with the known phenylamino- and pyridylamino-derivatives of 2,1,3-benzothiadiazole. It is found that the aryl substituent and noncovalent interactions affect the absorption band positions and emission in a solid and a solution. It is shown that under the mechanical action on polycrystalline samples of compounds 1 and 2 a hypsochromic shift of the emission band occurs, which indicates the weakening of noncovalent intermolecular interactions.

About the authors

T. S. Sukhikh

Nikolaev Institute of Inorganic Chemistry, Siberian Branch; Novosibirsk State University

Author for correspondence.
Email: sukhikh@niic.nsc.ru
Russian Federation, Novosibirsk; Novosibirsk

R. M. Khisamov

Nikolaev Institute of Inorganic Chemistry, Siberian Branch; Novosibirsk State University

Email: sukhikh@niic.nsc.ru
Russian Federation, Novosibirsk; Novosibirsk

D. A. Bashirov

Nikolaev Institute of Inorganic Chemistry, Siberian Branch; Novosibirsk State University

Email: sukhikh@niic.nsc.ru
Russian Federation, Novosibirsk; Novosibirsk

L. M. Kovtunova

Novosibirsk State University; Boreskov Institute of Catalysis, Siberian Branch

Email: sukhikh@niic.nsc.ru
Russian Federation, Novosibirsk; Novosibirsk

N. V. Kuratieva

Nikolaev Institute of Inorganic Chemistry, Siberian Branch; Novosibirsk State University

Email: sukhikh@niic.nsc.ru
Russian Federation, Novosibirsk; Novosibirsk

S. N. Konchenko

Nikolaev Institute of Inorganic Chemistry, Siberian Branch; Novosibirsk State University

Email: sukhikh@niic.nsc.ru
Russian Federation, Novosibirsk; Novosibirsk

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