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  4. Synthesis of linear unsubstituted poly(4,4′-triphenylamine) via Suzuki-Miyaura coupling of an asymmetric AB monomer
 
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Synthesis of linear unsubstituted poly(4,4′-triphenylamine) via Suzuki-Miyaura coupling of an asymmetric AB monomer

Publikationstyp
Journal Article
Date Issued
2022-06-15
Sprache
English
Author(s)
Kao, Tzu Han  
Qiao, Zhi  
Ho, Po Yuen 
Ditzer, Oliver  
Sun, Ningwei  
Voit, Brigitte  
Lissel, Franziska  
TORE-URI
http://hdl.handle.net/11420/15082
Journal
Journal of polymer science  
Volume
60
Issue
12
Start Page
1899
End Page
1911
Citation
Journal of Polymer Science 60 (12): 1899-1911 (2022-06-15)
Publisher DOI
10.1002/pol.20220016
Scopus ID
2-s2.0-85129733044
Polytriarylamines (PTAAs) are amorphous polymers that can be reversibly oxidized to generate stable radical cations. Despite exhibiting a low charge carrier mobility, PTAAs are widely used as hole-transporting layers in perovskite solar cells due to their excellent stability under ambient conditions. The highest occupied molecular orbital (HOMO) energy levels of PTAA are generally in the range of −5.1 to −5.2 eV, and therefore slightly too high for an optimal alignment with perovskites. Most linear PTAAs carry two or three methyl substituents per repeating unit. While these prevent crosslinking of chains and thus provide reaction control, the electron-donating substituents raise the energy level of the HOMO. Unsubstituted PTAA on the other hand is usually obtained crosslinked via oxidative polymerization, while nickel-catalyzed Grignard polycondensation leads to inclusion of impurities. We report the synthesis of linear unsubstituted PTAA using Suzuki-Miyaura coupling of a novel asymmetric monomer, 4-((4-bromophenyl)(phenyl)amino)phenyl)boronic acid M1. Based on matrix-assisted laser desorption/ionization-time of flight (MALDI-TOF) and 1H NMR analysis, we can conclude that the hydrogen-terminated linear polymer is obtained. The determined HOMO energy level of −5.47 eV is a favorable match for many perovskite systems.
Subjects
energy level
MALDI-TOF
polytriarylamine
Suzuki-Miyaura coupling
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