Perylene‐Embedded Helical Nanographenes with Emission up to 1010 nm: Synthesis, Structures, and Chiroptical Properties

Authors:
Publisher website
Google Scholar
Abstract
Near‐infrared (NIR) circularly polarized absorbing or emitting materials offer distinct advantages over their visible‐light counterparts and have attracted considerable interest across various fields. Materials exhibiting NIR chiroptical properties with high fluorescence quantum yields ( Φ F ) are particularly rare. In this study, we report the synthesis of a series of helical nanographenes ( 1 , 2 , 3 , and 4 ), where perylene is fused with one to four hexa‐ peri ‐hexabenzocoronene (sub) units by a strategy involving Diels–Alder cycloaddition followed by a Scholl reaction. X‐ray crystallographic analysis confirmed their structures, revealing helicene moieties integrated into a highly contorted framework. Benefiting from a similar distribution pattern of frontier molecular orbitals to perylene and extended π‐conjugation, compounds 1 – 4 demonstrate respectable Φ F values of 31.9 %, 15.0 %, 13.7 %, and 6.5 %, respectively, with emission maxima reaching up to 1010 nm. Their enantiopure forms, isolated by preparative chiral HPLC, exhibit distinct circular dichroism signals and circularly polarized luminescence across a broad spectral range, extending from the ultraviolet to the NIR.
Funding Information
  • Agency for Science, Technology and Research (M22K2c0083)
  • National Natural Science Foundation of China (92056203)
  • National Natural Science Foundation of China (22222110 and 22371206)

This publication has 54 references indexed in Scilit: