Expedient Synthesis of Substituted Thieno[3,2-b]thiophenes and Selenopheno[3,2-b]selenophenes Through Cascade Cyclization of Alkynyl Diol Derivatives
Thieno[3,2-b]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-b]thiophene and selenopheno[3,2-b]selenoph...
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| Published in | Molecules (Basel, Switzerland) Vol. 29; no. 23; p. 5507 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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| Abstract | Thieno[3,2-b]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-b]thiophene and selenopheno[3,2-b]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I2/Na2S2O3 or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials. |
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| AbstractList | Thieno[3,2-
b
]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-
b
]thiophene and selenopheno[3,2-
b
]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I
2
/Na
2
S
2
O
3
or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials. Thieno[3,2-b]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-b]thiophene and selenopheno[3,2-b]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I2/Na2S2O3 or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials. Thieno[3,2- ]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2- ]thiophene and selenopheno[3,2- ]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I /Na S O or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials. Thieno[3,2-b]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-b]thiophene and selenopheno[3,2-b]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I[sub.2]/Na[sub.2]S[sub.2]O[sub.3] or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials. |
| Audience | Academic |
| Author | He, Ziqing Zhao, Miaoshan Feng, Yingqi Zhang, Xuelin Chen, Lu Li, Yibiao Luo, Xiai |
| AuthorAffiliation | 2 Hunan Province Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, China 1 Jiangmen Key Laboratory of Synthetic Chemistry and Cleaner Production, School of Environmental & Chemical Engineering, Wuyi University, Jiangmen 529020, China; wyuchemfyq@126.com (Y.F.); wyuchemzxl@126.com (X.Z.); wyuchemhzq@126.com (Z.H.); wyuchemzms@126.com (M.Z.); wyuchemcl@126.com (L.C.) |
| AuthorAffiliation_xml | – name: 2 Hunan Province Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, China – name: 1 Jiangmen Key Laboratory of Synthetic Chemistry and Cleaner Production, School of Environmental & Chemical Engineering, Wuyi University, Jiangmen 529020, China; wyuchemfyq@126.com (Y.F.); wyuchemzxl@126.com (X.Z.); wyuchemhzq@126.com (Z.H.); wyuchemzms@126.com (M.Z.); wyuchemcl@126.com (L.C.) |
| Author_xml | – sequence: 1 givenname: Yingqi surname: Feng fullname: Feng, Yingqi – sequence: 2 givenname: Xuelin surname: Zhang fullname: Zhang, Xuelin – sequence: 3 givenname: Ziqing surname: He fullname: He, Ziqing – sequence: 4 givenname: Miaoshan surname: Zhao fullname: Zhao, Miaoshan – sequence: 5 givenname: Lu surname: Chen fullname: Chen, Lu – sequence: 6 givenname: Yibiao orcidid: 0000-0001-8249-5630 surname: Li fullname: Li, Yibiao – sequence: 7 givenname: Xiai surname: Luo fullname: Luo, Xiai |
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| Keywords | sulfur radical step-efficiency dehydration cyclization thienothiophene |
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| Snippet | Thieno[3,2-b]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors.... Thieno[3,2- ]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors.... Thieno[3,2- b ]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer... |
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| SubjectTerms | cyclization dehydration Efficiency Glycols Hydrocarbons Hydrogen Reagents Selenium Semiconductors step-efficiency Sulfur sulfur radical Temperature thienothiophene Thiophene |
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| Title | Expedient Synthesis of Substituted Thieno[3,2-b]thiophenes and Selenopheno[3,2-b]selenophenes Through Cascade Cyclization of Alkynyl Diol Derivatives |
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