Stack the Bowls: Tailoring the Electronic Structure of Corannulene‐Integrated Crystalline Materials

We report the first examples of purely organic donor–acceptor materials with integrated π‐bowls (πBs) that combine not only crystallinity and high surface areas but also exhibit tunable electronic properties, resulting in a four‐orders‐of‐magnitude conductivity enhancement in comparison with the par...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2018-08, Vol.130 (35), p.11480-11485
Main Authors: Rice, Allison M., Dolgopolova, Ekaterina A., Yarbrough, Brandon J., Leith, Gabrielle A., Martin, Corey R., Stephenson, Kenneth S., Heugh, Rebecca A., Brandt, Amy J., Chen, Donna A., Karakalos, Stavros G., Smith, Mark D., Hatzell, Kelsey B., Pellechia, Perry J., Garashchuk, Sophya, Shustova, Natalia B.
Format: Article
Language:English
Subjects:
Acceptor materials
Alkynes
Charge transfer
Chemistry
Corannulene
Crystal structure
Crystallinity
Cycloaddition
Electronic properties
Electronic structure
Immobilization
Kovalente organische Gerüstverbindungen
Leitfähigkeit
Optoelectronic devices
Photophysik
Theoretische Chemie
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We report the first examples of purely organic donor–acceptor materials with integrated π‐bowls (πBs) that combine not only crystallinity and high surface areas but also exhibit tunable electronic properties, resulting in a four‐orders‐of‐magnitude conductivity enhancement in comparison with the parent framework. In addition to the first report of alkyne–azide cycloaddition utilized for corannulene immobilization in the solid state, we also probed the charge transfer rate within the Marcus theory as a function of mutual πB orientation for the first time, as well as shed light on the density of states near the Fermi edge. These studies could foreshadow new avenues for πB utilization for the development of optoelectronic devices or a route for highly efficient porous electrodes. Eine π‐Schale wirft einen Blick in das Potentialenergiefenster für die Immobilisierung des Moleküls in einer Gerüststruktur. Die Integration von Corannulen resultierte in den ersten Beispielen rein organischer kristalliner poröser Materialien mit einstellbaren elektronischen Profilen und einer um vier Größenordnungen erhöhten Leitfähigkeit im Vergleich zum reinen Grundgerüst.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201806202