Rationalizing the photophysical properties of BODIPY laser dyes via aromaticity and electron-donor-based structural perturbations

Journal Article · Fri May 01 00:00:00 EDT 2015 · Dyes and Pigments

DOI:https://doi.org/10.1016/j.dyepig.2015.01.010· OSTI ID:1392384

Waddell, Paul G.; Liu, Xiaogang; Zhao, Teng; Cole, Jacqueline M.

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 Lab. (ANL), Argonne, IL (United States)
• Sponsoring Organization: USDOE Office of Science (SC), Basic Energy Sciences (BES)
• DOE Contract Number: AC02-06CH11357
• OSTI ID: 1392384
• Journal Information: Dyes and Pigments, Vol. 116, Issue C; ISSN 0143-7208
• Publisher: Elsevier
• Country of Publication: United States
• Language: English

Related Subjects

DFT
X-ray diffraction
absorption
fluorescence
optoelectronics
structure-property relationships