Impact of Substitution Position on the Photophysical Properties of Pyrrolidinone-Fused 1,2-Azaborines Chromophores
Disciplines
Chemistry | Materials Chemistry | Organic Chemistry | Physical Chemistry
Abstract (300 words maximum)
Flat-structured boron-nitrogen-containing heterocycles with extended conjugated π-systems such as pyrrolidinone-fused 1,2-azaborines (PFAs) are in high demand in the material and imaging technology markets because of their unique features such as simultaneous tunability of fluorescence color, extraordinary thermal and photochemical stability, high fluorescent quantum yields, and large Stokes shift. The incorporation of diverse electronic moieties at position 2 on the isoindolinone hemisphere of PFAs have previously shown to induce modification of the electronic transitions energies in the non-flexible π-systems. Herein, we have synthesized a series of novel PFAs substituted at position 1 to investigate the consequence of different substitution positions on the photophysical properties. Our studies have revealed that substitution at position 1 resulted in red-shifted absorbances along with a reduction in molar absorptivity when compared to the analogs substituted at position 2. We have also observed red-shifted emission in all solvents when compared to other analogs.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Carl Saint-Louis
Impact of Substitution Position on the Photophysical Properties of Pyrrolidinone-Fused 1,2-Azaborines Chromophores
Flat-structured boron-nitrogen-containing heterocycles with extended conjugated π-systems such as pyrrolidinone-fused 1,2-azaborines (PFAs) are in high demand in the material and imaging technology markets because of their unique features such as simultaneous tunability of fluorescence color, extraordinary thermal and photochemical stability, high fluorescent quantum yields, and large Stokes shift. The incorporation of diverse electronic moieties at position 2 on the isoindolinone hemisphere of PFAs have previously shown to induce modification of the electronic transitions energies in the non-flexible π-systems. Herein, we have synthesized a series of novel PFAs substituted at position 1 to investigate the consequence of different substitution positions on the photophysical properties. Our studies have revealed that substitution at position 1 resulted in red-shifted absorbances along with a reduction in molar absorptivity when compared to the analogs substituted at position 2. We have also observed red-shifted emission in all solvents when compared to other analogs.