TY - JOUR

T1 - Fluorescent mesoionic 1-(2-aryl-4H-thieno[3,4-d][1,2,3]triazol-2-ium-4-ylidene)ethan-1-olates: One-pot synthesis, photophysics, and biological behavior

AU - Eltyshev, Alexander K.

AU - Chernysheva, Nadezhda V.

AU - Minin, Artem S.

AU - Pozdina, Varvara A.

AU - Slepukhin, Pavel A.

AU - Benassi, Enrico

AU - Belskaya, Nataliya P.

N1 - Funding Information: EA and BN thanks RFBR for financially supporting this work through the project No 19-33-90184. The Siberian Branch of the Russian Academy of Sciences (SB RAS) Siberian Supercomputer Centre is gratefully acknowledged for providing supercomputer facilities. This work was performed using the equipment of the Shared Research Center of Scientific Equipment SRC IIP UrB RAS. Publisher Copyright: © 2021 Elsevier Ltd

PY - 2022/3

Y1 - 2022/3

N2 - This paper reports the one-pot synthesis of a rare type of mesoionic compounds, which are condensed mesoionics. A series of new bicyclic arylthienotriazoliumolates was synthesized by an improved synthetic method. This approach has a large scope of starting materials and was used to obtain diverse structures with outstanding photophysical properties. The pattern of substituents decorating the mesoionic ring was the important factor determining the electronic distributions of the synthesized compounds. Pull–pull (А–π–A), push–push (D–π–D), pull–push (A–π–D), and push–pull (D–π–A) systems were designed, synthesized and their absorption, emission, stability, and biological behavior were studied. Quantum chemical calculations were performed to deepen the knowledge about the absorption and emission properties of these systems and explain their unusual geometries and electronic structures. Confocal microscopy experiments showed that thienotriazoliumolates easily penetrated into living cells and selectively accumulated near the cell membrane, Golgi apparatus, and endoplasmic reticulum.

AB - This paper reports the one-pot synthesis of a rare type of mesoionic compounds, which are condensed mesoionics. A series of new bicyclic arylthienotriazoliumolates was synthesized by an improved synthetic method. This approach has a large scope of starting materials and was used to obtain diverse structures with outstanding photophysical properties. The pattern of substituents decorating the mesoionic ring was the important factor determining the electronic distributions of the synthesized compounds. Pull–pull (А–π–A), push–push (D–π–D), pull–push (A–π–D), and push–pull (D–π–A) systems were designed, synthesized and their absorption, emission, stability, and biological behavior were studied. Quantum chemical calculations were performed to deepen the knowledge about the absorption and emission properties of these systems and explain their unusual geometries and electronic structures. Confocal microscopy experiments showed that thienotriazoliumolates easily penetrated into living cells and selectively accumulated near the cell membrane, Golgi apparatus, and endoplasmic reticulum.

KW - DFT calculations

KW - Fluorescence

KW - Mesoionic heterocycles

KW - Oxidative cyclization

KW - Thienotriazole

UR - http://www.scopus.com/inward/record.url?scp=85118800172&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2021.109777

DO - 10.1016/j.dyepig.2021.109777

M3 - Article

AN - SCOPUS:85118800172

VL - 199

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 109777

ER -