Rationalizing the photophysical properties of BODIPY laser dyes via aromaticity and electron-donor-based structural perturbations
The absorption and fluorescence properties of six boron dipyrromethene (BODIPY) laser dyes with simple non-aromatic substituents are rationalized by relating them to observable structural perturbations within the molecules of the dyes. An empirical relationship involving the structure and the optical properties is derived using a combination of single-crystal X-ray diffraction data, quantum chemical calculations and electronic constants: i.e. the tendency of the pyrrole bond lengths towards aromaticity and the UV-vis absorption and fluorescence wavelengths correlating with the electron-donor properties of the substituents. The effect of molecular conformation on the solid-state optical properties of the dyes is also discussed. The findings in this study also demonstrate the usefulness and limitations of using crystal structure data to develop structure-property relationships in this class of optical materials, contributing to the growing effort to design optoelectronic materials with tunable properties via molecular engineering.
- Research Organization:
- Argonne National Laboratory (ANL)
- Sponsoring Organization:
- USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
- DOE Contract Number:
- AC02-06CH11357
- OSTI ID:
- 1392384
- Journal Information:
- Dyes and Pigments, Journal Name: Dyes and Pigments Journal Issue: C Vol. 116; ISSN 0143-7208
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
Similar Records
Tuning the photophysical properties of BODIPY dyes through extended aromatic pyrroles
Synthesis and Photochemical Properties of 2,3;5,6-bis(cyclohexano)-BODIPY