Coronenes, Benzocoronenes and Beyond: Modern Aspects of Their Syntheses, Properties, and Applications

Abstract

In recent years, a variety of new designs of coronene‐based polycyclic aromatic hydrocarbons (PAHs) with diverse functions have emerged to serve as complementary materials in organic chemistry and materials chemistry. In the present review, we highlight the modern aspects of syntheses related to or different from the strategies used in the early era of coronene research. Systematic extension and expansion of coronene backbones to wide categories of angular PAHs are covered. The substitution and extension of coronene architectures, by incorporating functional groups and by fusing small and large conjugated units, advatangeously enrich their photophysical, electrochemical, self‐assembling, and other properties, of which are discussed to demostrate their impact in materials chemistry. While the highly symmetric coronenes, tribenzocoronenes and hexabenzocoronenes conceived wide potential in charge‐transporting, electroluminescent, sensing, and other applications, other related derivatives such as dibenzo, tetrabenzo and pentabenzocoronenes also displayed their potentials as exemplified by their use as charge‐conduction channel in transistor application.

Synthesis, Structure, and Photophysical Properties of BN-Embedded Analogue of Coronene

“…Compound BN-Bzp was crystallized in the monoclinic space group P 2 1 / c , while compound BN-Cor was crystallized in the trigonal space group R 3̅ with 3̅ symmetry (Figure d). As presented in Figure and Table , the bond lengths in BNC 4 azaborine units are quite similar to reported structures in the literature for other azaborines. − The B or N involving bond lengths are obviously different from those of C–C bonds. For example, the bond length of B1–N1 in BN-Bzp and BN-Cor are very close (1.41 Å), much shorter than that of a B–N single bond (about 1.68 Å), and slightly longer than that of a localized BN double bond (1.403(2) Å), which supports the assignment of partial double-bond character.…”

“…Up to now, much effort has been devoted to developing BN-PAH analogues of benzene, naphthalene, anthracene, phenanthrene, pyrene, perylene, and others . Coronene is a typical peri-condensed PAH with D 6 h symmetry and is an important building block of optoelectronic materials . However, only a few examples of BN-embedded coronene derivatives have been reported (Figure ).…”

Multiple-boron–nitrogen (multi-BN) doped π-conjugated systems for optoelectronics

“…Coronene is also known as superbenzene, which contains seven peri-fused benzene rings, and an appealing building block of organic optoelectronic materials. 87 Multiple-BN unit-doped coronene and its derivatives have been paid more and more attention. Very recently, Liu, Yu and coworkers reported the synthesis of bis-BN-doped coronene 28 with two syn-paralleled BN units using a double BBr 3 -indued Scholl reaction.…”

Plasmonic Surface of Metallic Gold and Silver Nanoparticles Induced Fluorescence Quenching of Meso-Terakis (4-Sulfonatophenyl) Porphyrin (TPPS) and Theoretical–Experimental Comparable

“…The Perrin model was valid for the quenching process of TPPS by Ag NPs. The Perrin relationship [43] is given by Eq. ( 2):…”