Synthesis and Characterization of a Pentiptycene‐Derived Dual Oligoparaphenylene Nanohoop

Structural designs combining oligoparaphenylene‐derived nanohoops with other functional organic building blocks should lead to novel molecular architectures with intriguing properties. Herein, we describe the synthesis of a pentiptycene‐derived chiral dual nanohoop molecule with key steps including...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 58; no. 12; pp. 3943 - 3947
Main Authors Xu, Wei, Yang, Xiao‐Di, Fan, Xiang‐Bing, Wang, Xin, Tung, Chen‐Ho, Wu, Li‐Zhu, Cong, Huan
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 18.03.2019
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Crystal structure
Cycloaddition
Diels–Alder cycloaddition
Enantiomers
macrocycles
Molecular structure
nanohoops
oligoparaphenylenes
pentiptycenes
Physical Sciences
Science & Technology
CIRCULARLY-POLARIZED LUMINESCENCE
DESIGN
CARBON
nanohoops
pentiptycenes
PHOTOPHYSICAL PROPERTIES
Diels-Alder cycloaddition
PHOTODIMERIZATION
POLYMER-FILMS
STEREOISOMERISM
BELT
macrocycles
oligoparaphenylenes
CYCLOPARAPHENYLENES
BOTTOM-UP SYNTHESIS
Online AccessGet full text

Cover

More Information
Summary:Structural designs combining oligoparaphenylene‐derived nanohoops with other functional organic building blocks should lead to novel molecular architectures with intriguing properties. Herein, we describe the synthesis of a pentiptycene‐derived chiral dual nanohoop molecule with key steps including ring expansion through dianthracene cycloreversion and transannular [4+2] cycloaddition across a 64‐membered macrocycle. The crystal structure of the nanohoop molecule displays an ordered packing pattern with long‐range channels in the solid state. Furthermore, nonracemizable enantiomers of the nanohoop were obtained through resolution and exhibited promising chiroptical properties. Across the great divide: A pentiptycene‐derived chiral dual nanohoop has been synthesized through dianthracene cycloreversion followed by transannular cycloaddition across the resulting 64‐membered macrocycle (see scheme). The nanohoop molecule displays long‐range channels in the solid state and promising chiroptical properties after resolution.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
content type line 23
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201814482