Synthesis, characterization, and photophysical properties of some new thieno[2,3-b]pyridines bearing phenylethenyl moiety

被引：6

作者：

EL-Mahdy, Ahmed F. M. ^{[1
,2
]}

Bakhite, Etify A. ^{[1
]}

Abdel-Hafez, Shams H. ^{[3
]}

Ibrahim, Omaima F. ^{[1
]}

Abdu-Allah, Hajjaj H. M. ^{[4
]}

Marae, Islam S. ^{[1
]}

机构：

[1] Assiut Univ, Chem Dept, Fac Sci, Assiut 71516, Egypt

[2] Natl Sun Yat Sen Univ, Dept Mat & Optoelect Sci, Kaohsiung, Taiwan

[3] Taif Univ, Coll Sci, Dept Chem, At Taif, Saudi Arabia

[4] Assiut Univ, Fac Pharm, Dept Pharmaceut Organ Chem, Assiut, Egypt

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2022年 / 59卷 / 02期

关键词：

AGGREGATION-INDUCED EMISSION; DERIVATIVES; PHOSPHORESCENCE; PYRIDINES; SENSOR; AIE;

D O I：

10.1002/jhet.4391

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Acetyl-3-cyano-6-methyl-4-(2-phenylethenyl)pyridine-2(1H)-thione (2) was synthesized by interaction of cinnamylidene-2-cyanothioacetamide 1 and acetylacetone or via one-pot reaction of E-cinnamaldehyde, 2-cyanothioacetamide, and acetylacetone. Reaction of 2 with ethyl iodide (3a) or N-chloroacetyl derivative of aromatic amines 3b-e in boiling ethanol containing sodium ethoxide gave the corresponding thioether 4a and 5-acetyl-3-amino-2-(N-arylcarbamoyl)-6-methyl-4-(2-phenylethenyl)thieno[2,3-b]pyridines 5b-e, respectively. Compound 5e was reacted with 2,5-dimethoxytetrahydrofuran or triethyl orthoformate to furnish pyrrolylthienopyyridine 6 or pyrdiothienopyrimidinone 7, respectively. The photophysical properties of 5b, 5c, 5e, and 7 were fully studied and the obtained results included herein. The fluorescence data confirmed that compounds 5b, 5c, 5e, and 7 exhibit aggregation-induced emission behavior with high absolute quantum yields.

引用

页码：359 / 370

页数：12

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