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Updated: Jul 21, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

パルフローロサイクロブチル結合ヘクサ・ペリ・ヘクサベンゾコロネンネットワーク

Bryan K Spraul1, S Suresh, Sibylle Glaser

  • 1Center for Optical Materials Science and Engineering Technologies (COMSET), Department of Chemistry and School of Materials Science and Engineering, Clemson University, Clemson, SC 29634, USA.

Journal of the American Chemical Society
|October 8, 2004
PubMed
まとめ

研究者らは,新型のトリフローロビニルエーテル置換ヘクサ・ペリ・ヘクサベンゾコロネン (HBC) を合成し,それをパーフローロサイクロブチル (PFCB) ポリマーにポリマー化しました. このブレークスルーは,処理可能なHBC光学材料を提供し,以前の溶解性の課題を克服しています.

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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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