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Synthesizing Strained Azatriseptane Frameworks


Zhang, Kai; El Bitar Nehme, Mélissa; Hope, Philip A; Rickhaus, Michel (2023). Synthesizing Strained Azatriseptane Frameworks. Helvetica Chimica Acta, 106(4):e202200195.

Abstract

Embedding seven-membered rings into polycyclic aromatic molecules is attractive as they can exert an influence on molecular conformation that ultimately changes the solubility and π-electronics. The considerations in designing and synthesizing a highly strained azatriseptane framework is discussed herein. We employ a twofold macrocyclization strategy to form the [7,7,7]-system and through scoping various strategies identify a Friedel–Crafts approach is key. The synthetic limitations we have identified, in addition to the successes presented here, highlights the key challenges in forming triseptane frameworks and paves the way for second-generation analogues that may have various applications in optical as well as electronic organic materials.

Abstract

Embedding seven-membered rings into polycyclic aromatic molecules is attractive as they can exert an influence on molecular conformation that ultimately changes the solubility and π-electronics. The considerations in designing and synthesizing a highly strained azatriseptane framework is discussed herein. We employ a twofold macrocyclization strategy to form the [7,7,7]-system and through scoping various strategies identify a Friedel–Crafts approach is key. The synthetic limitations we have identified, in addition to the successes presented here, highlights the key challenges in forming triseptane frameworks and paves the way for second-generation analogues that may have various applications in optical as well as electronic organic materials.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Inorganic Chemistry, Organic Chemistry, Physical and Theoretical Chemistry, Drug Discovery, Biochemistry, Catalysis
Language:English
Date:1 April 2023
Deposited On:09 Jan 2023 09:02
Last Modified:28 Apr 2024 01:42
Publisher:Wiley Open Access
ISSN:1522-2675
OA Status:Green
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/hlca.202200195
Project Information:
  • : FunderSwiss National Science Foundation
  • : Grant IDPZ00P2_180101
  • : Project Title
  • Content: Accepted Version
  • Language: English