Two-Step Synthetic Route to BODIPY Dyes for Solar Cell Applications

Two-Step Synthetic Route to BODIPY Dyes for Solar Cell Applications

Presenter(s)

John Connor Quinn

Description

Dye Sensitized Solar Cells (DSSCs) are beginning to show great promise as an alternative energy source, but the cost and lack of efficiency of most current dyes remains a problem. A series of BODIPY dyes have been synthesized by a two-step synthetic route to provide a solution. A dipyrrin was formed through the reaction of either napthyl[1,2-c]pyrrole or fluorantho[2,3-c]pyrrole with one of several aromatic aldehydes in a solid state reaction. The resulting dipyrrins were reacted with boron trifluoride to give a series of highly conjugated BODIPY dyes. Upon analyzing the photophysical properties of the dyes with UV-VIS and fluorescence spectroscopy, it was found that using the more highly conjugated fluoranthro[2,3-c]pyrrole to form the dipyrrin core results in a favorable red shift of about 50 nm, as compared to more modest shifts as a result of changing the aldehyde. Cyclic voltametry also demonstrated a stabilization of the LUMO energy of the dyes formed from the more highly conjugated pyrrole. All of the dyes display molar absorptivities greater than 100 000 M−1 cm−1 with photoluminescence quantum efficiencies of 0.5–1.0, and the HOMO and LUMO energies of the dyes further illustrate the suitability of these dyes for use in DSSCs.

Publication Date

4-5-2017

Project Designation

Independent Research - Undergraduate

Primary Advisor

Shawn M. Swavey

Primary Advisor's Department

Chemistry

Keywords

Stander Symposium project

Two-Step Synthetic Route to BODIPY Dyes for Solar Cell Applications

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