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Tetrakis(phenylethynyl)tetracene: A New π‐Extended Rubrene Derivative
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- Kei Kitamura
- Department of Applied Chemistry for Environment Kwansei Gakuin University 2-1 Gakuen Sanda 669-1337 Japan
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- Kenta Asahina
- Department of Applied Chemistry for Environment Kwansei Gakuin University 2-1 Gakuen Sanda 669-1337 Japan
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- Yusaku Nagai
- Department of Applied Chemistry for Environment Kwansei Gakuin University 2-1 Gakuen Sanda 669-1337 Japan
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- Haruki Sugiyama
- Department of Chemistry School of Science Tokyo Institute of Technology, Ookayama 2 Meguro-ku Tokyo 152-8551 Japan
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- Hidehiro Uekusa
- Department of Chemistry School of Science Tokyo Institute of Technology, Ookayama 2 Meguro-ku Tokyo 152-8551 Japan
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- Toshiyuki Hamura
- Department of Applied Chemistry for Environment Kwansei Gakuin University 2-1 Gakuen Sanda 669-1337 Japan
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Description
<jats:title>Abstract</jats:title><jats:p>An efficient synthetic route to 5,6,11,12‐tetrakis(arylethynyl)tetracenes, new π‐extended rubrene derivatives, was developed by means of [2+4] cycloaddition of dialkynylnaphthalyne and dialkynylisobenzofuran. Importantly, two alkynyl groups introduced into the aryne exerts a significant effect in lowering the LUMO energy, allowing practical access to sterically overcrowded polycyclic structures through an efficient HOMO–LUMO interaction. Study on the potential reactivity inherent in the <jats:italic>peri</jats:italic>‐ethynyl‐substituted tetracenes revealed several interesting reactivities. X‐ray analysis of these new π‐extended derivatives showed distorted structures to reduce steric repulsion due to the existence of the substituents at the <jats:italic>peri</jats:italic>‐positions.</jats:p>
Journal
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- Chemistry – A European Journal
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Chemistry – A European Journal 24 (53), 14034-14038, 2018-09-12
Wiley
