Twisted Diindeno-Fused Dibenzo[a,h]anthracene Derivatives and their Dianions

Gu，Yanwei1,3; Torchon，Herdya S.2; Zhu，Yikun2; Wei，Zheng2; Schollmeyer，Dieter5; Wagner，Manfred1; Ni，Yong6; Wu，Zehua1; Wu，Hao1; Zhou，Yazhou1; Qiu，Zijie1; Petrukhina，Marina A.2; Müllen，Klaus1,4

2023-08-21

10.1002/anie.202307750

Angewandte Chemie - International Edition   影响因子和分区

1433-7851

1521-3773

We 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-2Ph and DIDBA-2H, 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.

Aromaticity Dianions Diradicals Fused-Ring Systems Twisted Structures

SCI ; EI

英语

NI论文

其他

National Science Foundation[CHE-2003411];U.S. Department of Energy[DE-AC02-06CH11357];National Science Foundation[NSF/CHE-1834750];

Chemistry

Chemistry, Multidisciplinary

WOS:001027502700001

WILEY-V C H VERLAG GMBH

20232914406820

Anthracene ; Density functional theory ; Electronic structure ; X ray crystallography

Organic Compounds:804.1 ; Probability Theory:922.1 ; Atomic and Molecular Physics:931.3 ; Quantum Theory; Quantum Mechanics:931.4 ; Crystal Lattice:933.1.1

CHEMISTRY

2-s2.0-85164806067

Scopus

1.Synthetic Chemistry,Max Planck Institute for Polymer Research,Mainz,Ackermannweg 10,55128,Germany
2.Department of Chemistry,University at Albany,State University of New York,Albany,1400 Washington Ave,12222,United States
3.Ningbo Institute of Materials Technology & Engineering,Chinese Academy of Sciences,Ningbo,Zhejiang,315201,China
4.Institute for Physical Chemistry,Johannes Gutenberg University Mainz,Mainz,Duesbergweg 10–14,55128,Germany
5.Department of chemistry,Johannes Gutenberg University Mainz,Mainz,Duesbergweg 10–14,55128,Germany
6.Department of Chemistry,Southern University of Science and Technology,Shenzhen,Guangdong,518055,China

Gu，Yanwei,Torchon，Herdya S.,Zhu，Yikun,et al. Twisted Diindeno-Fused Dibenzo[a,h]anthracene Derivatives and their Dianions[J]. Angewandte Chemie - International Edition,2023,62(34).

Gu，Yanwei.,Torchon，Herdya S..,Zhu，Yikun.,Wei，Zheng.,Schollmeyer，Dieter.,...&Müllen，Klaus.(2023).Twisted Diindeno-Fused Dibenzo[a,h]anthracene Derivatives and their Dianions.Angewandte Chemie - International Edition,62(34).

Gu，Yanwei,et al."Twisted Diindeno-Fused Dibenzo[a,h]anthracene Derivatives and their Dianions".Angewandte Chemie - International Edition 62.34(2023).