Affiliation:
1. Synthetic Chemistry Max Planck Institute for Polymer Research Ackermannweg 10 55128 Mainz Germany
2. Ningbo Institute of Materials Technology & Engineering Chinese Academy of Sciences Ningbo Zhejiang 315201 P. R. China
3. Department of Chemistry University at Albany State University of New York 1400 Washington Ave Albany NY 12222 USA
4. Department of chemistry Johannes Gutenberg University Mainz Duesbergweg 10–14 55128 Mainz Germany
5. Department of Chemistry Southern University of Science and Technology Shenzhen Guangdong 518055 P. R. China
6. Institute for Physical Chemistry Johannes Gutenberg University Mainz Duesbergweg 10–14 55128 Mainz Germany
Abstract
AbstractWe report a facile synthesis of diindeno‐fused dibenzo[a,h]anthracene derivatives (DIDBA‐2Cl, DIDBA‐2Ph, and DIDBA‐2H) with different degrees of non‐planarity using three substituents (chloro, phenyl, and hydrogen) of various sizes. The planarization of their cores, as evidenced by the decreased end‐to‐end torsional angles, was confirmed by X‐ray crystallography. Their enhanced energy gaps with twisting were investigated by a combination of spectroscopic and electrochemical methods with density functional theory, which showed a transition from singlet open‐shell to closed‐shell configuration. Moreover, their doubly reduced states, DIDBA‐2Ph2− and DIDBA‐2H2−, were achieved by chemical reduction. The structures of dianions were identified by X‐ray crystallographic analysis, which elucidated that the electron charging further distorted the backbones. The electronic structure of the dianions was demonstrated by experimental and theoretical approaches, suggesting decreased energy gaps with larger non‐planarity, different from the neutral species.
Funder
Max-Planck-Gesellschaft
H2020 European Research Council
Gutenberg Forschungskolleg
Alexander von Humboldt-Stiftung
National Science Foundation
U.S. Department of Energy
Subject
General Chemistry,Catalysis
Cited by
1 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献