Probing Peripheral H-Bonding Functionalities in BN-Doped Polycyclic Aromatic Hydrocarbons.

Area of Science:

• Supramolecular Chemistry
• Materials Science
• Organic Chemistry

Background:

• Polycyclic aromatic hydrocarbons (PAHs) are crucial in materials science.
• Heteroatom doping, specifically with boron-nitrogen (BN) triads, offers new functional possibilities.
• The hydrogen-bonding capabilities of BN-doped PAHs have not been previously investigated.

Purpose of the Study:

• To synthesize and study the solution recognition of peripherally NBN-doped PAH isosteres.
• To investigate the formation of hydrogen-bonded complexes using these novel molecules.
• To quantify the association strengths of these complexes.

Main Methods:

• Synthesis of peripherally NBN-doped benzo[fg]tetracenyl derivatives.
• Solution recognition studies using complementary H-bonding partners.
• Determination of association constants (Ka) via NMR spectroscopy in deuterated solvents (C6D6, CDCl3).

Main Results:

• Successfully formed H-bonded DD·AA- and ADDA·DAAD-type complexes.
• Quantified 1:1 association strengths: ~27 M⁻¹ for DD·AA in C6D6 and ~1820 M⁻¹ for ADDA·DAAD in CDCl3.
• Demonstrated the H-bonding potential of BN mimics of amidic NH functions in PAHs.

Conclusions:

• Peripherally NBN-doped PAHs can effectively form supramolecular complexes through hydrogen bonding.
• The strength of H-bonding varies significantly with complex type and solvent.
• These findings open avenues for designing novel materials with tailored organizational properties using BN-doped PAHs.