Synthesis and characterization of pyrimidine-containing hexaarylbenzene derivatives

Zhang, Dengqing; Wang, Gang; Chen, Huafu; Li, Xianying; Xiang, Yucheng; Zhang, Zhen; Jin, Wusong

doi:10.1039/c5ra18422c

Cited by 5 publications

(2 citation statements)

References 45 publications

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“…198 The purpose of the introduction of carboxylic groups is to enhance the degree of hydrogen bonding, metal-binding abilities, and self-assembly properties. Similar to the previous report, 197 isomers 105 and 106 (Figure 52) were produced from cyclotrimerization of respective unsymmetrical 1,2-disubstituted acetylene. The flocculant nanostructures of derivatives 105 turned into beltlike structures after interaction with Ag + ions, which led to a red-shift in the emission band, whereas no such switching in aggregates or shift in emission band were observed in the case of derivative 106.…”

Section: Chemical Reviewssupporting

confidence: 86%

“…Recently, Zhang et al 197 reported synthesis of pyrimidinecontaining HPB derivatives 102−104 (Figure 52) through cyclotrimerization of appropriate disubstituted acetylenes. The symmetric 1,2-disubstituted acetylene resulted in formation of a single major product 102, whereas unsymmetrical 1,2-disubstituted counterparts produced two isomers, 103 and 104, under similar conditions.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold

2016

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The easily rotatable peripheral aromatic rings around central benzene in hexaarylbenzene (HAB) derivatives create a very intriguing nonplanar, propeller-shaped geometry. Because of the very low susceptibility toward self-aggregation, HAB derivatives are much stronger candidates among various polyphenylenes/hetero-oligophenylenes when poor molecular cohesion and inefficient packing is required. However, the native properties of hexaphenylbenzene (HPB) can be varied by proper tailoring and substitution of the HAB core. The cohesion and packing in the structures of HAB aggregates induce effective structural variations so as to modify the fundamental features. Recently, HAB derivatives attracted a lot of research interest because of their significant role as liquid crystalline materials, organic light-emitting diodes, photochemical switches, redox materials, and molecular receptors. Herein, detailed attention is given to the pioneering work based on synthetic optimization of different HAB cores, elaborated study of their crystal engineering, various interesting applications of HAB derivatives, and future possibilities and capabilities of this still underexplored scaffold.

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Section: Chemical Reviewssupporting

confidence: 86%

Section: Chemical Reviewsmentioning

confidence: 99%

Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold

2016

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Synthesis of Distorted Nitrogen‐Doped Nanographenes by Partially Oxidative Cyclodehydrogenation Reaction

Varghese

Gao

Chang

et al. 2022

Chemistry An Asian Journal

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A series of partially fused N‐doped nanographenes (2–4) are synthesized via the oxidative cyclodehydrogenation of oligoaryl‐substituted dibenzo[e,l]pyrene (1), and five, six, and seven new C−C bonds are formed, respectively, implying stepwise C−C bond fusion and extended π‐conjugation. Single‐crystal X‐ray diffraction analysis of compound 4 a revealed that the presence of sterically demanding groups hindered the formation of planar and fully fused nanographene in the oxidative cyclodehydrogenation reaction step. Optical study of compounds 2 to 4 showed that extended π‐conjugation leads to a regular stepwise bathochromic shift in the absorption and emission spectra. Furthermore, the HOMO–LUMO gaps of these compounds exhibit a decrease as C−C bond formation proceeds. Thus, the optoelectronic properties of nanographenes are highly dependent on the formation of new C−C bonds in the molecular skeleton.

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Ruthenium(II)-Catalyzed Microwave-Promoted Multiple C–H Activation in Synthesis of Hexa(heteroaryl)benzenes in Water

et al. 2018

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A series of hexa(heteroaryl)benzenes were synthesized by the Ru(II)-carboxylate-catalyzed multiple C-H activation of benzenes carrying pyridyl, pyrimidyl, or pyrazolyl directing groups using N-heteroaryl bromides as coupling partners. The reactions proceeded with high selectivity under microwave irradiation in water. Iterative penta-arylation could be implemented via activation of C-H bonds of generated intermediates by cascade chelation assistance of in situ installed pyridyl groups. This strategy provides multidentate ligands for selective complexation of transition metals and potential building of photoredox systems.

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Synthesis and characterization of pyrimidine-containing hexaarylbenzene derivatives

Abstract: Three claw-shaped hexaarylbenzene derivatives containing pyrimidines have been synthesized by cobalt-catalyzed corresponding tolan derivatives.

Cited by 5 publications

References 45 publications

Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold

Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold

Synthesis of Distorted Nitrogen‐Doped Nanographenes by Partially Oxidative Cyclodehydrogenation Reaction

Ruthenium(II)-Catalyzed Microwave-Promoted Multiple C–H Activation in Synthesis of Hexa(heteroaryl)benzenes in Water

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