Photochemical Synthesis of 4H-Thieno[3,2-c]chromene and Their Optical Properties

Evgeny B. Ulyankin; Yulia P. Bogza; Anastasia S. Kostyuchenko; Sergey A. Chernenko; Anna L. Samsonenko; Anton L. Shatsauskas; Vyacheslav L. Yurpalov; Alexander S. Fisyuk

doi:10.1055/a-1392-2209

Synlett, Table of Contents

Synlett 2021; 32(08): 790-794
DOI: 10.1055/a-1392-2209

letter

Photochemical Synthesis of 4H-Thieno[3,2-c]chromene and Their Optical Properties

Evgeny B. Ulyankin

^aLaboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050, Omsk, Russian Federation

,

Yulia P. Bogza

^bDepartment of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077, Omsk, Russian Federation

,

Anastasia S. Kostyuchenko

^aLaboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050, Omsk, Russian Federation

^bDepartment of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077, Omsk, Russian Federation

,

Sergey A. Chernenko

^aLaboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050, Omsk, Russian Federation

,

Anna L. Samsonenko

^bDepartment of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077, Omsk, Russian Federation

,

Anton L. Shatsauskas

^bDepartment of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077, Omsk, Russian Federation

,

Vyacheslav L. Yurpalov

^cCenter of New Chemical Technologies BIC, 54 Neftezavodskaya St., 644040 Omsk, Russian Federation

,

Alexander S. Fisyuk∗

^aLaboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050, Omsk, Russian Federation

› Author Affiliations

Abstract

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Abstract

4-{[(2-Iodoaryl)oxy]methyl}thiophene-2-carbaldehydes and 5-iodo-4-(aryloxymethyl)thiophene-2-carbaldehydes were obtained by the reaction of phenols with 4-(chloromethyl)thiophene-2-carbaldehyde or its 5-iodo analogue, respectively. These products underwent ring closure upon irradiation with UV light (254 nm) to form the corresponding 4H-thieno[3,2-c]chromene-2-carbaldehydes in high yield. The formation of intermediate radical species was detected by EPR spectroscopy. Comparative analysis of ring-closure methods showed that photochemical cyclization of 5-iodo-4-(aryloxymethyl)thiophene-2-carbaldehyde is superior to Pd-catalyzed intramolecular arylation. A series of substituted 4H-thieno[3,2-c]chromene-2-carbaldehydes were synthesized by the photochemical cyclization of the corresponding precursors, and the photophysical properties of the products were studied. The 4H-thieno[3,2-c]chromene-2-carbaldehydes can be used as covert marking pigments.

Key words

photochemistry - cyclization - thienochromenes - luminescence - arylation - pigments

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References

References and Notes

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