Helicene Chemistry From Synthesis to Applications
This book systematically reviews recent advances in the synthetic methods and applications of helicenes. The first part of this book introduces the nomenclature and structural features of helicenes. The second part reviews several classic and useful metho
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licene Chemistry From Synthesis to Applications
Helicene Chemistry
Chuan-Feng Chen Yun Shen •
Helicene Chemistry From Synthesis to Applications
123
Chuan-Feng Chen Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry Chinese Academy of Sciences Beijing China
ISBN 978-3-662-53166-2 DOI 10.1007/978-3-662-53168-6
Yun Shen Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry Chinese Academy of Sciences Beijing China
ISBN 978-3-662-53168-6
(eBook)
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Preface
Compared with other chiral molecules, helicenes, comprised of ortho-fused aromatics, bear helicity and p-conjugated structures. Because of the highly contorted p-surfaces with superior chiroptical properties, synthetic challenges for the diversity of the skeletons, interesting interaction behaviors between themselves or with other (chiral) molecules, the helicene chemistry has been attracting more and more attention. Since the first report in 1903, it has been developed for more than 110 years. In 1950s, the helical structure was unambiguously demonstrated by X-ray crystallographic analysis. Moreover, the optical resolution was achieved and the relationship between the absolute configuration and chiroptical property was established. Some practical synthetic methods have been discovered, especially in the last three decades, such as metal-mediated [2+2+2] triynes cycloisomerization, Diels–Alder addition, and oxidative photocyclization. Some reactions render the preparation in gram scale, and some reactions could afford helicenes even in >99 % ee. Due to the advances in preparation, diffe
