Benzdiynes and Related Dehydroaromatics

Tadatake Sato; Hiroyuki Niino

doi:10.1071/CH10044

RESEARCH FRONT

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Benzdiynes and Related Dehydroaromatics

Tadatake Sato ^A ^B and Hiroyuki Niino ^A

+ Author Affiliations

- Author Affiliations

^A Photonics Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan.

^B Corresponding author. Email: sato-tadatake@aist.go.jp

Dr Tadatake Sato was born in Japan. He received his Ph.D. degree (1998) from Kyoto University. He is working as a research scientist in the National Institute of Advanced Industrial Science and Technology (AIST) since 1998. His research interests are characterization of reactive species using low-temperature matrix isolation technique, and laser-processing of transparent materials and its application.

Dr Hiroyuki Niino was born in Japan. He received his Ph.D. degree (1994) from Kyushu University. He is working as a research scientist in the National Institute of Advanced Industrial Science and Technology (AIST) since 1987. At present, he is a group leader of the laser-induced materials processing group in AIST. His research interests are laser ablation and chemical processing of materials by lasers.

Australian Journal of Chemistry 63(7) 1048-1060 https://doi.org/10.1071/CH10044
Submitted: 24 January 2010 Accepted: 15 April 2010 Published: 15 July 2010

Abstract

Benzdiynes, which are more unsaturated than benzyne, were proposed as reactive intermediates in the pyrolyses of aromatic dianhydrides in 1966. The generation and direct observation of these highly unsaturated species has been an experimental challenge. More than 30 years later, the first direct observation of a benzdiyne, 1,4-bis(trifluoromethyl)-2,3,5,6-tetradehydrobenzene, was reported. We outline the progress in the generation and observation of benzdiynes as well as theoretical studies on the background of benzyne chemistry. Spectroscopic observation of the benzdiynes, in particular detection of an IR band due to the asymmetric stretching of the two triple bonds, in conjunction with quantum chemical computations reveals their multireference character. In connection with the studies for generating benzdiynes, the studies for generating bisarynes with extended π-systems and the most highly unsaturated cyclic C₆ are briefly reviewed.

Acknowledgements

We are deeply indebted to Dr A. Yabe and Dr Moriyama: the experimental studies on benzdiyne were started by Dr A. Yabe together with Dr M. Moriyama. We are also indebted to Dr S. Arulmozhiraja and Dr T. Uchimaru for theoretical studies on benzdiynes. We thank Dr T. Matsuura and S. Sasaki of NTT Advanced Technology Inc. and Professor Masakazu Ohkita of Nagoya Institute of Technology for supplying the dianhydride precursors. This work was supported in part by Japan’s Ministry of Education, Culture, Sports, Science, and Technology, Center of Excellence Development (COE) Project, and Grants-in-Aid for Young Scientists (B) (No.17750445) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

References

Benzdiynes and Related Dehydroaromatics

Abstract

Acknowledgements

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