1. Comparison of Meso-Substituted BODIPY Cores with Activated
and Deactivated Phenyl Ring Substituents
Muntaser Farooque, Malek El-Aooiti , Sidra Sabagh, Hardeep Devgan, and Bryan D. Koivisto*
Department of Chemistry and Biology, Ryerson University, 350 Victoria Street, Toronto ON, Canada, M5B 2K3
Chemistry and Biology Department – Third Annual Research Symposium – Wednesday, August 20th, 2014
The dye-sensitized solar cell (DSSC) is a type of next-generation
photovoltaic cell which allows harvesting of renewable solar energy in an
efficient and economical way. An organic dye molecule is the powerhouse of
this solar cell. The dye consists of a three parts; a donor, a conjugated linker
and an acceptor (D-p-A). By tuning these three components, one can
optimize energy transfer and light-harvesting.
Figure 1: (D-p-A), Thiophene as the p-spacer. Figure 2: (D-p-A), BODIPY as the p-spacer.
Introduction
Methods: Synthesis of a Variety of Meso Position
Substituted BODIPY Cores
BODIPY (4,4’-difluoro-4-bora-3a,4a-diaza-s-indacene) is an ubiquitous
molecule that can be used for this application. It is also low cost from
commercially available starting materials. The molecule can be
modified in a variety of ways to increase its already high extinction
coefficient which entails desirable solar cell performance.
2
Meso
6
Figure 3: Configurable positions on the BODIPY molecule
Electrochemistry Characterization: Cyclic
Voltammetry
Table 1: Electrochemical data for the varied BODIPYs
data collected in DCM using 0.1 M [nBu4N][PF6] at 100 mV/s and
referenced to a [Fc]/[Fc]+ internal standard (+ 765 mV vs. NHE in
DCM)
1H-NMR Characterization: Aromatic Region of the
BODIPYs CDCl3
CH2Cl2
UV-Vis Characterization: Optical Properties
Table 2: Data collected from the UV-Vis spectra for each BODIPY core.
Acknowledgements
We are very grateful to Burhan Hussein and Ben Fischer for their
assistance and guidance throughout the summer. A huge thank you to
Bryan Koivisto for allowing us to have this great opportunity and gain
valuable lab experience.
Compound Ered Eox
Nitro Phenyl BODIPY -0.726 1.62
Phenyl BODIPY -0.957 1.52
Anisole Phenyl BODIPY -0.977 1.54
Trimethoxy Phenyl BODIPY - 1.58
Compound ʎmax ( nm) ɛ (M-1
cm-1
)
Nitro Phenyl BODIPY 506 60000
Phenyl BODIPY 501 48000
Anisole Phenyl BODIPY 501 78000
Trimethoxy Phenyl BODIPY 502 55000
2
2
2
2