English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse
  1. View item / 
  2. Item Summary

Item

ITEM ACTIONSEXPORT
Add to Basket
  Local TagsRelease HistoryDetailsSummary

Released
Journal Article

Modular Synthesis of Structurally Diverse Azulene-Embedded Polycyclic Aromatic Hydrocarbons by Knoevenagel-Type Condensation

MPS-Authors
/persons/resource/persons287894

Ma,  Ji       
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

/persons/resource/persons47863

Feng,  Xinliang       
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

External Resource

https://doi.org/10.1002/anie.202219091
(Publisher version)

Fulltext (restricted access)
There are currently no full texts shared for your IP range.
Fulltext (public)

Angew Chem Int Ed-2023-Liu.pdf
(Publisher version), 6MB

Supplementary Material (public)
There is no public supplementary material available
Citation

Liu, R., Fu, Y., Wu, F., Liu, F., Zhang, J.-J., Yang, L., et al. (2023). Modular Synthesis of Structurally Diverse Azulene-Embedded Polycyclic Aromatic Hydrocarbons by Knoevenagel-Type Condensation. Angewandte Chemie, International Edition in English, 62(21): e202219091. doi:10.1002/anie.202219091.


Cite as: https://hdl.handle.net/21.11116/0000-000D-480F-3
Abstract
The research interest in azulene-embedded polycyclic aromatic hydrocarbons (PAHs) has significantly increased recently, but the lack of efficient synthetic strategies impedes the investigation of their structure-property relationships and further opto-electronic applications. Here we report a modular synthetic strategy towards diverse azulene-embedded PAHs by a tandem Suzuki coupling and base-promoted Knoevenagel-type condensation with good yields and great structural versatility, including non-alternant thiophene-rich PAHs, butterfly- or Z-shaped PAHs bearing two azulene units, and the first example of a two-azulene-embedded double [5]helicene. The structural topology, aromaticity and photophysical properties were investigated by NMR, X-ray crystallography analysis and UV/Vis absorption spectroscopy assisted by DFT calculations. This strategy provides a new platform for rapidly synthesizing unexplored non-alternant PAHs or even graphene nanoribbons with multiple azulene units.