Novel porphyrin polymers: synthesis and photoelectric property
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Novel porphyrin polymers: synthesis and photoelectric property Jianfeng Ban1,*, Shaoxiong Xu2, and Lulu Pan1 1 2
School of Materials Science and Engineering, Guangdong University of Petrochemical Technology, Maoming 525000, China Guangzhou Occupational Disease Prevention Hospital, Guangzhou 510000, China
Received: 7 May 2020
ABSTRACT
Accepted: 7 September 2020
A series of novel porphyrin monomers with different tail lengths were synthesized through the Alder–Longo method, and the corresponding polymers were successfully synthesized via radical polymerization. The structures of the porphyrin monomers and polymers were all depicted through proton nuclear magnetic resonance (1H-NMR) and matrix-assisted laser desorption ionizationtime of flight (MALDI-TOF) mass spectrometry, and the photophysical and electrochemical properties were confirmed through UV–Vis spectroscopy, photoluminescence spectroscopy, and cyclic voltammetry. The results showed that the polymers exhibited a deep highest occupied molecular orbital (HOMO) energy level and a large optical band gap, demonstrating their usefulness in photovoltaic devices. All of the porphyrin monomers formed a typical columnar phase, and the cleaning point of these porphyrin monomers reduced with the increasing length of the alkoxy tail chain. Thermogravimetric analysis demonstrated that the polymers had excellent thermal stability; the decomposition temperature was higher than 400 °C. The UV absorption spectrum of the polymers was between 400 and 670 nm. Compared with the absorption peak of the solution, the absorption peak after film formation presented a certain redshift. The HOMO level was lower than the stable critical level of the conjugated polymer in air (- 5.2 eV), indicating that the polymer is stable in air. In addition, the lowest unoccupied molecular orbital energy level was 0.49–0.64 eV, which was higher than that of the recipient PCBM, indicating that the polymers can be used as a donor material for solar cells.
Published online: 22 September 2020
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Springer Science+Business
Media, LLC, part of Springer Nature 2020
Handling Editor: Gregory Rutledge.
Address correspondence to E-mail: [email protected]
https://doi.org/10.1007/s10853-020-05333-8
J Mater Sci (2021) 56:1814–1826
Introduction Porphyrins are a class of natural compounds with strong dyeing properties and several important biological abilities (for example, they are involved in oxygen transport and photosynthesis) [1–3]. Porphyrins have been one of the important topics to study in solar cells, due to the unique molecular structure, which leads to extraordinary chemical, and optical properties [4, 5]. They have aroused extensive research interest in the fields of chemical adsorption and separation organic [6, 7], photovoltaic [8–10], catalysis [11, 12], biomedicine [13, 14], and anticancer drug manufacturing [15, 16]. Porphyrin derivatives and polymers are some of the most studied materials in recent years. The conversion efficiencies of porphyrin dye-based solar cells are among the best r
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