학술논문
A Combination of B‐ and N‐Doped π‐Systems Enabling Systematic Tuning of Electronic Structures and Properties.
Document Type
Article
Source
Subject
*DOPING agents (Chemistry)
*INTRAMOLECULAR charge transfer
*POLYCYCLIC aromatic hydrocarbons
*INTRAMOLECULAR proton transfer reactions
*LEWIS bases
*LEWIS acidity
*ELECTRONIC structure
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Language
ISSN
0947-6539
Abstract
Doping heteroatoms into polycyclic aromatic hydrocarbons (PAHs) may alter their structures and thereby physical properties. This study reports the construction of B/N‐codoped PAHs via combining the B‐ and N‐doped π‐systems. Two π‐extended B/N‐codoped PAHs were synthesized through the Mallory photoreaction. Both feature a C48BN2 π‐skeleton, which is assembled by linearly fusing three substructures including B‐doped and sp2‐hybridized N‐doped π‐moieties and one pyrene unit. In comparison to the pristine B‐doped analog, their intramolecular charge transfer (ICT) states are distinctly modulated by the fused N‐doped π‐system and the further incorporated cyano group, leading to their tunable optical properties, as revealed by detailed theoretical and experimental analysis. Furthermore, these three molecules have sufficient Lewis acidity and can coordinate with Lewis base to form Lewis acid‐base adducts, and notably, such intermolecular complexation can further dynamically modulate their ICT transitions and thereby photophysical properties, such as producing blue, green and red fluorescence. [ABSTRACT FROM AUTHOR]