The copper-catalyzed synthesis of (Z)-2H-naphtho[1,8-bc]thiophenes with solid emission

In recent years, one of the main research interests of our group has been the construction of 6/5 π-systems through the regioselective conversion of parallel alkynes in naphthalene with the aim of exploiting potential fluorescent materials. Herein, the copper-catalyzed synthesis of polysubstituted (...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-02, Vol.19 (8), p.1827-1834
Main Authors: Zhang, Yuan, Lai, Weiping, Zhang, Lianpeng, Gao, Xiaoxing, Qiu, Guanyinsheng, Zhou, Hongwei
Format: Article
Language:English
Subjects:
Alkynes
Chemical synthesis
Copper
Crystallography
Deuteration
Emission
Fluorescence
Naphthalene
Optoelectronics
Potassium
Selectivity
Sulfur
Thiophenes
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Summary:In recent years, one of the main research interests of our group has been the construction of 6/5 π-systems through the regioselective conversion of parallel alkynes in naphthalene with the aim of exploiting potential fluorescent materials. Herein, the copper-catalyzed synthesis of polysubstituted (Z)-2H-naphtho[1,8-bc]thiophenes from 8-halo-1-ethynylnaphthalenes using potassium ethylxanthate as the sulfur source is reported. In this protocol, a series of thiophene-fused 6/5 π-system compounds was synthesized via copper-catalyzed Ullmann-type C(aryl)–S bond formation and the α-addition of an alkyne bond with high selectivity and in high yields. The synthesized polysubstituted (Z)-2H-naphtho[1,8-bc]thiophenes exhibited solid emission, which made them potential candidates for use in optoelectronic conjugated materials. By using DMSO/D2O (3 : 1) as the reaction solvent, the deuterated products could be obtained in good yields under standard conditions.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02233k