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Updated: Jun 14, 2025
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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
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COMPAS-4: A Data Set of (BN)1 Substituted Cata-Condensed Polybenzenoid Hydrocarbons─Data Analysis and Feature
Sabyasachi Chakraborty1, Itay Almog1, Renana Gershoni-Poranne1
1The Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis, Technion - Israel Institute of Technology, Haifa 32000, Israel.
Journal of Chemical Information and Modeling
|May 23, 2025
Summary
Researchers developed principles for designing boron-nitrogen (BN) substituted polycyclic aromatic hydrocarbons (PBHs) with specific electronic properties. The most influential structural feature identified is the number of disturbed cyclic delocalization rings in the molecule.
Area of Science:
- Computational Chemistry
- Materials Science
- Organic Chemistry
Background:
- Boron-nitrogen (BN) pair incorporation into polycyclic aromatic hydrocarbons (PBHs) is a known method for tuning electronic properties.
- A clear framework for understanding and predicting these structure-property relationships in BN-PBHs is currently lacking.
- Generalizable principles for the rational design of BN-substituted PBHs are needed.
Purpose of the Study:
- To establish concrete principles for the rational design of (BN)1-PBHs with tailored electronic properties.
- To develop a data-driven approach for understanding BN-substitution effects in PBHs.
- To identify key structural features governing the properties of BN-PBHs.
Main Methods:
- Construction of a new chemical database, COMPAS-4, containing isomers of (BN)1-PBHs up to 6 rings.
- Calculation of molecular geometries and properties using GFN1-xTB and density functional theory (DFT) (CAM-B3LYP/def2-SVP).
- Analysis of the influence of BN-substitution on molecular orbital energies and aromaticity.
Main Results:
- Identification of specific, chemically intuitive structural features that dictate the electronic properties of BN-PBHs.
- Demonstration that these features can be extracted directly from molecular structures without prior computation.
- Finding that the number of rings with disturbed cyclic delocalization is the most significant factor influencing properties.
Conclusions:
- The study provides a quantitative framework for understanding BN-substitution effects in PBHs.
- The identified structure-property relationships enable the rational design of BN-PBHs for targeted applications.
- The number of disrupted delocalized rings serves as a key predictive indicator for molecular properties.
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