Hexa-peri-benzocoronene with two extra K-regions in an ortho-configuration. Issue 47 (26th October 2020)

• Record Type: Journal Article
• Authors: Dumslaff, Tim; Gu, Yanwei; Paternò, Giuseppe M.; Qiu, Zijie; Maghsoumi, Ali; Tommasini, Matteo; Feng, Xinliang; Scotognella, Francesco; Narita, Akimitsu; Müllen, Klaus
• Is Part Of: Chemical science. Volume 11:Issue 47(2020)
• Page Start: 12816
• Page End: 12821
• Publication Date: 2020-10-26
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc04649c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We reported the synthesis of hexa- peri -benzocoronene (HBC) with two extra K-regions adopting an ortho -configuration. The systematical study provides deep insights about the effect of zigzag edge on the π-conjugated pathway and molecular design. Abstract : There are three possible isomers for hexa- peri -hexabenzocoronene (HBC) with two extra K-regions, but only two of them have been reported, namely with the meta - and para -configurations. Herein, we describe the synthesis of HBC 4 with two extra K-regions in the ortho -configuration, forming a longer zigzag edge compared with the other two isomers. The structure of 4 was validated by laser desorption/ionization time-of-flight mass analysis and nuclear magnetic resonance spectra, as well as Raman and infrared spectroscopies supported by density functional theory calculations. The optical properties of 4 were investigated by UV/vis absorption and ultrafast transient absorption spectroscopy. Together with the analysis of aromaticity, the influence of the zigzag edge on the π-conjugation pathway and HOMO–LUMO gaps of the three isomers were investigated.