Engineering Polycyclic 1,2-BN-Heteroarenes for Stimuli-Responsive Materials via Electron-Deficient Heterocycle Substitutions
Disciplines
Materials Chemistry | Organic Chemistry | Physical Chemistry
Abstract (300 words maximum)
Polycyclic aromatic hydrocarbons are valued for strong absorption and fluorescence, and their modification with B–N bonds yields planar aromatic azaborines with tunable optoelectronic properties. Incorporation of nitro groups (–NO₂) into polycyclic 1,2-BN heteroarenes (PBNHs) produces electron-deficient n-type conjugates that display red-shifted spectra but often suffer from aggregation-caused quenching (ACQ) of emission. We previously showed that twisted molecular geometries suppress ACQ in –NO₂ substituted PBNHs and induce aggregation-induced emission (AIE). However, these designs still exhibited poor solubility and diminished optical performance. In this work, we integrate electron-deficient heterocycles (EDHs), including benzodiazole, benzothiadiazole, and benzoselenadiazole derivatives, into the PBNH scaffold to overcome these limitations. EDH substitution improves solubility, preserves key photophysical features, and introduces multi-stimuli responsiveness. Spectroscopic studies reveal solvatochromism, improved solid-state fluorescence, thermochromism, and halochromism, highlighting their environmental sensitivity. Furthermore, EDH-PBNHs were successfully applied in proof-of-concept stimuli-responsive devices, such as rewritable and self-erasable papers. This study demonstrates a versatile strategy for engineering electron-deficient BN-heteroarenes with enhanced solubility, tunable emission, and multifunctional responsiveness. These findings expand the potential of BN-based materials for advanced optoelectronics, sensing, and adaptive device technologies.
Use of AI Disclaimer
no
Academic department under which the project should be listed
CSM – Chemistry and Biochemistry
Primary Investigator (PI) Name
Carl J. Saint-Louis
Engineering Polycyclic 1,2-BN-Heteroarenes for Stimuli-Responsive Materials via Electron-Deficient Heterocycle Substitutions
Polycyclic aromatic hydrocarbons are valued for strong absorption and fluorescence, and their modification with B–N bonds yields planar aromatic azaborines with tunable optoelectronic properties. Incorporation of nitro groups (–NO₂) into polycyclic 1,2-BN heteroarenes (PBNHs) produces electron-deficient n-type conjugates that display red-shifted spectra but often suffer from aggregation-caused quenching (ACQ) of emission. We previously showed that twisted molecular geometries suppress ACQ in –NO₂ substituted PBNHs and induce aggregation-induced emission (AIE). However, these designs still exhibited poor solubility and diminished optical performance. In this work, we integrate electron-deficient heterocycles (EDHs), including benzodiazole, benzothiadiazole, and benzoselenadiazole derivatives, into the PBNH scaffold to overcome these limitations. EDH substitution improves solubility, preserves key photophysical features, and introduces multi-stimuli responsiveness. Spectroscopic studies reveal solvatochromism, improved solid-state fluorescence, thermochromism, and halochromism, highlighting their environmental sensitivity. Furthermore, EDH-PBNHs were successfully applied in proof-of-concept stimuli-responsive devices, such as rewritable and self-erasable papers. This study demonstrates a versatile strategy for engineering electron-deficient BN-heteroarenes with enhanced solubility, tunable emission, and multifunctional responsiveness. These findings expand the potential of BN-based materials for advanced optoelectronics, sensing, and adaptive device technologies.