New Potential Fluorogenic Dyes with an Extended π-System Based on Arylidene-Azolones

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Abstract

We propose a new series of 19 potential fluorogenic dyes with an increased system of conjugated bonds based on arylidene-imidazolones and arylidene-rhodanines. The optical properties of the synthesized compounds were studied. We demonstrated that new substances are characterized by a noticeable bathochromic shift of absorption and emission maxima, as well as a remarkable Stokes shift and a significant FQY variation depending on the properties of the environment. The obtained arylallylideneimidazolones and arylallylidene-rhodanines can be potentially used in fluorescence microscopy for selective staining of living cell organelles.

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About the authors

S. A. Krasnova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; National Research University Higher School of Economics

Author for correspondence.
Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Myasnitskaya 20, Moscow, 101000

A. V. Eshtukov-Shcheglov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS

Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. Y. Smirnov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University

Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

Y. A. Bogdanova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University

Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

M. S. Baranov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry RAS; Pirogov Russian National Research Medical University

Email: svetlanakr2002@mail.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997; ul. Ostrovitianova 1, Moscow, 117997

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3. Scheme 1. General scheme of synthesis of arylallidene imidazolones (IIIa–IIIi) and arylallidene rhodanines (IVb–IVk).

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