Date of Award

Spring 4-2-2026

Document Type

Distinction Paper

Degree Name

Chemistry-BS

Department

Chemistry

Advisor

Grace Eder

First Committee Member

Grace Eder

Second Committee Member

Dean Johnston

Third Committee Member

Steffanie Burk

Keywords

Polymeric materials, Azadipyrromethene, Chemistry, Synthesis, Organics, Organic Dyes

Subject Categories

Higher Education | Organic Chemistry | Other Chemistry | Polymer Chemistry

Abstract

Azadipyrromethene (ADP) is an organic dye molecule that absorbs red light.1 ADPs have potential to be used in organic photovoltaics (OPVs) as an electron acceptor molecule because of its extensive amount of conjugated pi-bonds, tunability, and absorption of near infrared (IR) light. These qualities make ADP an acceptor that is very complementary to commonly used OPV electron donor molecules, such as poly(3- hexylthiophene) (P3HT).2

One of the main setbacks of OPVs, is the fact they have lower power conversion efficiencies (PCEs) than already commercially available cells. Improving the donor and acceptor compositions of OPVs is an area of study that may improve PCEs.3 Covalent organic frameworks (COFs) are a type of polymer that has been used in OPVs to try and resolve poor PCEs.4 Developing an ADP-based COF will enhance ADP’s validity as an acceptor molecule for OPVs.  Using synthesis techniques including Fischer esterification, aldol condensation, and a Michael reaction both a reduced ADP-OH and a homoleptic Zn(ADP-OH)2 complex were synthesized. A final oxidation step would provide Zn(ADP-CHO)2 ready for inclusion in a COF. With attempts to perform this oxidation, an understanding of the challenges of oxidizing both ADP-OH and the homoleptic Zn(ADP-OH)2 complex were revealed. With an inability to oxidize either of the two alterations to an initial reaction scheme were made to feature an acetal protecting group which would eliminate the need for oxidation. Over the course of the synthesis of these ADPs difficult purifications arose and purification protocols were optimized.

Licensing Permission

Copyright, all rights reserved. Fair Use

Acknowledgement 1

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Acknowledgement 2

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