A Combination of B‐ and N‐Doped π‐Systems Enabling Systematic Tuning of Electronic Structures and Properties

Author:

Sun Wenting1,Yang Yue1,Tian Xinyu1,Yuan Liuzhong1,Wang Yue1,Dou Chuandong12ORCID

Affiliation:

1. State Key Laboratory of Supramolecular Structure and Materials College of Chemistry Jilin University Changchun 130012 P. R. China

2. Jiangsu Engineering Laboratory of Novel Functional Polymeric Materials Soochow University Suzhou 215123 P. R. China

Abstract

AbstractDoping 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.

Funder

Jilin Provincial Scientific and Technological Development Program

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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