Synthesis, Characterization, and Properties of BN-Fluoranthenes
Erlong Li1, Mengjia Jin2, Ruijun Jiang1
1School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, People's Republic of China.
Organic Letters
|June 22, 2022
Summary
New boron/nitrogen-doped fluoranthenes were synthesized using C-H borylation. These BN-fluoranthenes exhibit wider energy gaps and undergo cross-coupling reactions, expanding possibilities for novel materials.
Area of Science:
- Organic Chemistry
- Materials Science
- Supramolecular Chemistry
Background:
- Fluoranthenes are polycyclic aromatic hydrocarbons with unique electronic properties.
- Doping polycyclic aromatic hydrocarbons with boron and nitrogen offers a route to tune their optoelectronic characteristics.
- Developing novel synthetic methodologies for heteroatom-doped aromatic systems is crucial for advanced materials discovery.
Purpose of the Study:
- To synthesize a new class of boron/nitrogen-doped fluoranthenes.
- To investigate the functionalization and properties of these novel BN-fluoranthene derivatives.
- To explore the impact of BN-doping on the electronic structure and aromaticity of fluoranthenes.
Main Methods:
- Synthesis of BN-doped fluoranthenes via pyrrolic-type nitrogen directed C-H borylation.
- Regioselective bromination of BN-fluoranthene intermediates.
- Utilizing halogenated BN-fluoranthenes in various cross-coupling reactions.
- Experimental and computational studies to quantify aromaticity and electronic properties.
Main Results:
- Successful synthesis of BN-doped fluoranthenes, a novel class of cyclopenta-fused polycyclic aromatic hydrocarbons.
- Generation of mono- and dibrominated BN-fluoranthenes through regioselective bromination.
- Demonstration of cross-coupling reactions on halogenated BN-fluoranthenes to create diverse derivatives.
- Observation of wider HOMO-LUMO energy gaps in BN-fluoranthene compared to undoped counterparts.
- Quantification of aromaticity in BN-fluoranthene using both experimental and computational approaches.
Conclusions:
- Pyrrolic-type nitrogen directed C-H borylation is an effective method for synthesizing BN-doped fluoranthenes.
- BN-doping significantly modifies the electronic properties of fluoranthenes, leading to wider energy gaps.
- The synthesized BN-fluoranthenes serve as versatile building blocks for further functionalization via cross-coupling reactions.
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