Issue 30, 2022

meso-Ethynyl-extended push–pull type porphyrins for near-infrared organic photodetectors

Abstract

Natural porphyrins play a key role in a range of vital functions such as oxygen transport in the bloodstream and the conversion of light to chemical energy in plants. Likewise, synthetic porphyrin derivatives can be used to detect light and convert it into an electrical current in photodiodes. The versatility of porphyrinoid chemistry allows to extend the absorptivity (and hence detectivity) to the near-infrared while maintaining good solubility, suitable electrochemical properties, and compatibility with the electron acceptor molecules required to achieve a reasonable photocurrent. Here, our efforts on the design and synthesis of novel push–pull type meso-ethynyl-extended porphyrin compounds, both of A–D–A and D–A–D type (D = donor, A = acceptor), and their evaluation in prototype near-infrared organic photodetector devices are presented. The push–pull design with strongly electron-deficient building blocks results in absorption onsets up to 1200 nm, translating in an optical gap approaching 1 eV. Both A–D–A and D–A–D small molecules show good photodetector performance, with a peak specific detectivity near 2 × 1011 and 4 × 1011 Jones at 1000 nm (at −2 V bias), respectively. These values are among the best reported so far for small molecule based near-infrared organic photodetectors.

Graphical abstract: meso-Ethynyl-extended push–pull type porphyrins for near-infrared organic photodetectors

Supplementary files

Article information

Article type
Paper
Submitted
11 Feb 2022
Accepted
07 Jul 2022
First published
08 Jul 2022

J. Mater. Chem. C, 2022,10, 10853-10859

Author version available

meso-Ethynyl-extended push–pull type porphyrins for near-infrared organic photodetectors

S. Gielen, V. C. Gómez, S. Brebels, T. J. Quill, J. Vanderspikken, L. Lutsen, P. de la Cruz, K. Vandewal, F. Langa and W. Maes, J. Mater. Chem. C, 2022, 10, 10853 DOI: 10.1039/D2TC00588C

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