Molecular Carbon Imides

Abstract

The creation and development of new forms of nanocarbons have fundamentally transformed the scientific landscape in the past three decades. As new members of the nanocarbon family with accurate size, shape, and edge structure, molecular carbon imides (MCIs) have shown unexpected and unique properties. Particularly, the imide functionalization strategy has endowed these rylene-based molecular carbons with fascinating characteristics involving flexible syntheses, tailor-made structures, diverse properties, excellent processability, and good stability. This Perspective elaborates molecular design evolution to functional landscapes, and illustrative examples are given, including a promising library of multi-size and multi-dimensional MCIs with rigidly conjugated π-architectures, ranging from 1D nanoribbon imides and 2D nanographene imides to cross-dimensional MCIs. Although researchers have achieved substantial progress in using MCIs as functional components for exploration of charge transport, photoelectric conversion, and chiral luminescence performances, they are far from unleashing their full potential. Developing highly efficient and regioselective coupling/ring-closure reactions involving the formation of multiple C–C bonds and the annulation of electron-deficient aromatic units is crucial. Prediction by theory with the help of machine learning and artificial intelligence research along with reliable nanotechnology characterization will give an impetus to the blossom of related fields. Future investigations will also have to advance towardor even focus onthe emerging potential functions, especially in the fields of chiral electronics and spin electronics, which are expected to open new avenues.

Supramolecularly Engineered Bulk‐Heterojunction Solar Cells with Self‐Assembled Non‐Fullerene Nanographene Tetraimide Acceptors

“…The molecular highest occupied molecular orbital (HOMO) and LUMO levels were experimentally determined by CV for 1a and 1b [ 24 ] in CH 2 Cl 2 ( c 0 = 2 × 10 −5 m ) with added Bu 4 NPF 6 (0.1 m ) and calibrated against the ferrocene/ferrocenium (Fc/Fc + ) couple. Five reversible reduction potentials were observed and the first reduction potential ( E ½ Red1 ) at ≈−1.02 ( 1a ) and −1.04 V ( 1b ) of the PAH tetraimides equals the one of unsubstituted PBIs with −1.02 V [ 29 ] which resemble both LUMO levels at about −4.1 eV with Fc/Fc + value of –5.15 eV [ 30 ] vs. vacuum (Figure 1b, S11, and Table S3, Supporting Information). The first oxidation potential ( E ½ Ox1 ) at +1.02 V leads to an electrochemical bandgap of 2.06 eV, which is well in accordance with the optical bandgap determined from the onset of the tailing short‐wavelength absorption band (2.0 eV).…”

Advances in Molecular Design and Photophysical Engineering of Perylene Bisimide-Containing Polyads and Multichromophores for Film-Based Fluorescent Sensors

“…Recent years have witnessed various PBI derivatives with fascinating properties governed by divergent photophysical behaviors, enabling significant applications ranging from photovoltaics, photodetectors, and emitting materials. These contents have been extensively reviewed elsewhere. − In the context of a created molecular platform based on bottom-up chemical synthesis, PBI-containing polyads and multichromophores are emerging as promising organic optoelectronic materials, whereby several modular molecular entities are covalently or noncovalently integrated into one system in different distances and orientations via molecular engineering or supramolecular interactions. If the composed molecular entities are different, for example, D-A, D 1 -A-D 2 , A 1 -D-A 2 , D 1 -D 1 -A-D 2 , etc.…”

Nitrogen-doped polycyclic aromatic hydrocarbons by a one-pot Suzuki coupling/intramolecular SNAr reaction

“…Thus, we anticipate that the new class of Ndoped imide-functionalized PAHs provides an important extension of the structural and functional space of so-far explored imide-functionalized PAHs and nanographenes. 23,24…”