BOPHYs versus BODIPYs: A comparison of their performance as effective multi-function organic dyes

Area of Science:

• Organic Chemistry
• Photophysics
• Materials Science

Background:

• BODIPY dyes are well-established but have limitations.
• BOPHY dyes offer a versatile scaffold for tuning photophysical properties.
• Understanding BOPHY strengths and weaknesses is crucial for developing new dyes.

Purpose of the Study:

• To computationally and experimentally investigate BOPHY photophysical and lasing properties.
• To compare BOPHYs with BODIPY counterparts under various conditions.
• To explore BOPHY chemical versatility for targeted applications like red-emitting, chiroptical, and photosensitizer dyes.

Main Methods:

• Computational modeling of photophysical properties.
• Experimental characterization of BOPHY derivatives.
• Comparative analysis of BOPHY and BODIPY dye families.
• Exploration of BOPHY scaffold modifications (e.g., BINOLation, bromination, alkylation).

Main Results:

• BOPHY BINOLation with enantiopure BINOLs induces chiroptical activity but reduces fluorescence via ICT.
• Alkylation of the BOPHY core effectively modulates ICT, leading to bright BINOL-based BOPHY dyes.
• Brominated BOPHYs facilitate singlet oxygen generation through heavy-atom effect-mediated spin-orbit coupling.

Conclusions:

• Established design guidelines for creating bright fluorophores, laser dyes, photosensitizers, and chiroptical dyes based on BOPHYs.
• BOPHYs demonstrate tunable properties, allowing for a balance of functionalities within a single molecular scaffold.
• BOPHYs present a promising alternative to BODIPY dyes, offering competitive performance and versatility.