scholarly journals Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)

2020 ◽  
Vol 16 ◽  
pp. 530-536 ◽  
Author(s):  
Anping Luo ◽  
Min Zhang ◽  
Zhangyi Fu ◽  
Jingbo Lan ◽  
Di Wu ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Functional Groups ◽  
Aromatic Hydrocarbons ◽  
Precious Metal ◽  
Metal Catalysts ◽  
Optoelectronic Materials ◽  
Precious Metal Catalysts ◽  
Polycyclic Aromatic ◽  
Organic Optoelectronic

The regioselective C–H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) is a desired but challenging task. A copper-catalyzed C7–H arylation of 1-naphthamides has been developed by using aryliodonium salts as arylating reagents. This protocol does not need to use precious metal catalysts and tolerates wide variety of functional groups. Under standard conditions, the remote C–H arylation of other PAHs including phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3-carboxamide has also accomplished, which provides an opportunity for the development of diverse organic optoelectronic materials.

scholarly journals Copper-Catalyzed Remote C–H Arylation of Polycyclic Aromatic Hydrocarbons (PAHs)

2020 ◽  
Author(s):  
Anping Luo ◽  
Min Zhang ◽  
Zhangyi Fu ◽  
Jingbo Lan ◽  
Di Wu ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Functional Groups ◽  
Aromatic Hydrocarbons ◽  
Precious Metal ◽  
Metal Catalysts ◽  
Optoelectronic Materials ◽  
Precious Metal Catalysts ◽  
Polycyclic Aromatic ◽  
Organic Optoelectronic

The regioselective C–H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) is a desired but challenging task. Herein, a copper-catalyzed C7–H arylation of 1-naphthamides has been developed by using aryliodonium salts as arylating reagents. This protocol does not need to use precious metal catalysts and can tolerate wide functional groups. Under standard conditions, the remote C–H arylation of other PAHs including phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3-carboxamide has also accomplished, which provides an opportunity for the development of diverse organic optoelectronic materials.

scholarly journals Access tetracoordinate boron-doped polycyclic aromatic hydrocarbons with aggregation-induced emission under mild conditions

2021 ◽  
Author(s):  
Long Jiang ◽  
Dehui Tan ◽  
Xiaobin Chen ◽  
Tinghao Ma ◽  
Baoliang Zhang ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Functional Groups ◽  
Aromatic Hydrocarbons ◽  
Coupling Reactions ◽  
Optoelectronic Materials ◽  
Aggregation Induced Emission ◽  
Boron Doped ◽  
Polycyclic Aromatic ◽  
The Difference ◽  
Oxidative Coupling Reactions

The boron-doped polycyclic aromatic hydrocarbons (PAHs) have attracted ongoing attention in the field of optoelectronic materials due to their unique optical and redox properties. To investigate the effect of tetracoordinate boron in PAHs bearing N-heterocycles (indole and carbazole), a facile approach to four-coordinate boron-doped PAHs was developed, which does not require elevated temperature and pre-synthesized functionalized boron reactants. Five tetracoordinate boron-doped PAHs (NBNN-1 – NBNN-5) were synthesized with different functional groups. Two of them (NBNN-1 and NBNN-2) could further undergo oxidative coupling reactions to form fused off-plane tetracoordinate boron-doped PAHs NBNN-1f and NBNN-2f. Compared to the three-coordinate boron-doped counterparts, the UV/Vis absorption and fluorescent emission are significantly red-shift. Unlike the distinct impact of coordination number of boron on optoelectronic properties, the difference of functional groups on the boron atom has negligible impact on their optical and electrochemical properties. The compounds NBNN-1f and NBNN-2f show aggregation-induced emission.

scholarly journals Synthesis and Properties of NitroHPHAC: The First Example of Substitution Reaction on HPHAC

Molecules ◽  
2020 ◽  
Vol 25 (11) ◽  
pp. 2486
Author(s):  
Yoshiki Sasaki ◽  
Masayoshi Takase ◽  
Shigeki Mori ◽  
Hidemitsu Uno
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Charge Transfer ◽  
Functional Groups ◽  
Radical Cation ◽  
Aromatic Hydrocarbons ◽  
Substitution Reaction ◽  
Intramolecular Charge Transfer ◽  
Direct Introduction ◽  
Polycyclic Aromatic

Hexapyrrolohexaazacoronene (HPHAC) is one of the N-containing polycyclic aromatic hydrocarbons in which six pyrroles are fused circularly around a benzene. Despite the recent development of HPHAC analogues, there is no report on direct introduction of functional groups into the HPHAC skeleton. This work reports the first example of nitration reaction of decaethylHPHAC. The structures of nitrodecaethylHPHAC including neutral and two oxidized species (radical cation and dication), intramolecular charge transfer (ICT) character, and global aromaticity of the dication are discussed.

Quantifying the equilibrium partitioning of substituted polycyclic aromatic hydrocarbons in aerosols and clouds using COSMOtherm

2017 ◽  
Vol 19 (3) ◽  
pp. 288-299 ◽  
Author(s):  
Boluwatife Awonaike ◽  
Chen Wang ◽  
Kai-Uwe Goss ◽  
Frank Wania
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Functional Groups ◽  
Aromatic Hydrocarbons ◽  
Environmental Fate ◽  
Parent Compound ◽  
Equilibrium Partitioning ◽  
Polycyclic Aromatic

Functional groups attached to polycyclic aromatic hydrocarbons (PAHs) can significantly modify the environmental fate of the parent compound.

Imides modified benzopicenes: synthesis, solid structure and optoelectronic properties

2014 ◽  
Vol 12 (44) ◽  
pp. 8902-8910 ◽  
Author(s):  
Di Wu ◽  
Haojie Ge ◽  
Zhao Chen ◽  
Jinhua Liang ◽  
Jie Huang ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Optoelectronic Properties ◽  
Optoelectronic Materials ◽  
Solid Structure ◽  
Polycyclic Aromatic

Imide-modified polycyclic aromatic hydrocarbons can be widely applied in the field of optoelectronic materials.

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