Photochemical Synthesis of 4H-Thieno[3,2-c]chromene and Their Optical Properties | Sciact - CRIS-system of Boreskov Institute of Catalysis

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

Journal

Synlett
ISSN: 0936-5214

Output data

Year: 2021, Volume: 32, Number: 08, Pages: 790-794 Pages count : 5 DOI: 10.1055/a-1392-2209

Tags

photochemistry - cyclization - thienochromenes - luminescence - arylation - pigments

Authors

Ulyankin Evgeny B. ¹ , Bogza Yulia P. ² , Kostyuchenko Anastasia S. ^1,2 , Chernenko Sergey A. ¹ , Samsonenko Anna L. ² , Shatsauskas Anton L. ² , Yurpalov Vyacheslav L. ³ , Fisyuk Alexander S. ¹

Affiliations

1	Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave, 644050, Omsk, Russian Federation
2	Department of Organic Chemistry, Omsk F.M. Dostoevsky State University, 55a Mira Ave, 644077, Omsk, Russian Federation
3	Center of New Chemical Technologies BIC, 54 Neftezavodskaya St., 644040 Omsk, Russian Federation

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.

Ulyankin E.B. , Bogza Y.P. , Kostyuchenko A.S. , Chernenko S.A. , Samsonenko A.L. , Shatsauskas A.L. , Yurpalov V.L. , Fisyuk A.S.
Photochemical Synthesis of 4H-Thieno[3,2-c]chromene and Their Optical Properties
Synlett. 2021. V.32. N08. P.790-794. DOI: 10.1055/a-1392-2209 WOS Scopus РИНЦ ANAN OpenAlex publication_identifier_short.sciact_ihcp_identifier_type

Submitted:	Jan 16, 2021
Accepted:	Feb 16, 2021
Published online:	Feb 16, 2021
Published print:	May 1, 2021

Web of science:	WOS:000626718500001
Scopus:	2-s2.0-85102487937
Elibrary:	46761406
Chemical Abstracts:	2021:627431 \| 174:782586
OpenAlex:	W3132742041
publication_identifier.sciact_ihcp_identifier_type:	3463

DB	Citing
Scopus	4
Web of science	3
OpenAlex	6
Elibrary	7