Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules
by
Stefania Aivali 1, Loukia Tsimpouki 1, Charalampos Anastasopoulos 1,2 and Joannis K. Kallitsis 1,2,*
Stefania Aivali 1, Loukia Tsimpouki 1, Charalampos Anastasopoulos 1,2 and Joannis K. Kallitsis 1,2,*
1
Department of Chemistry, University of Patras, University Campus, Rio-Patras GR26504, Greece
2
Foundation for Research and Technology Hellas/Institute of Chemical Engineering Sciences (FORTH/ICE-HT), Platani Str., Patras GR26504, Greece
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(23), 4406; https://doi.org/10.3390/molecules24234406
Received: 1 November 2019 / Revised: 27 November 2019 / Accepted: 30 November 2019 / Published: 2 December 2019
Perylene diimide (PDI) is one of the most studied functional dyes due to their structural versatility and fine tuning of the materials properties. Core substituted PDIs are prominent n-type semiconductor materials that could be used as non-fullerene acceptors in organic photovoltaics. Herein, we develop versatile organic building blocks based on PDI by decorating the PDI core with quinoline groups. Styryl and hydroxy phenyl mono and difunctionalized molecules were prepared using mono-nitro and dibromo bay substituted PDIs by Suzuki coupling with the respective boronic acid derivatives. A novel methodology using nitro-PDI under Suzuki coupling conditions as an electrophile partner was successfully tested. Furthermore, the PDI derivatives were used for the synthesis of soluble, electron accepting small molecules combining PDI with weak electron withdrawing quinoline derivatives. The new molecules presented wide absorbance in the visible spectrum from 450 to almost 700 nm while their LUMO levels and their energy levels are in the range of −3.8 to −4.2 eV.
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Keywords:
functional perylene; Suzuki reaction; non fullerene acceptors; electrochemical and optical properties
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MDPI and ACS Style
Aivali, S.; Tsimpouki, L.; Anastasopoulos, C.; Kallitsis, J.K. Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules. Molecules 2019, 24, 4406.
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