journal article·2020-03-25Open access

Synthesis of Poly(bisisoindigo) Using a Metal-Free Aldol Polymerization for Thin-Film Transistor Applications

Anindya Ganguly, Keqiang He, Arthur D. Hendsbee, Maged Abdelsamie, Raymond N. Bennett, Yuning Li, Michael F. Toney, Timothy L. Kelly

ACS Applied Materials & Interfaces· Volume 12· Issue 12

Abstract

Typical syntheses of conjugated polymers rely heavily on organometallic reagents and metal-catalyzed cross-coupling reactions. Here, we show that an environmentally benign aldol polymerization can be used to synthesize poly(bisisoindigo), an analog of polyisoindigo with a ring-fused structural repeat unit. Owing to its extended conjugation length, poly(bisisoindigo) absorbs across the UV/vis/NIR spectrum, with an absorption tail that reaches 1000 nm. Due to the four electron-deficient lactam units on each repeat unit, poly(bisoindigo) possesses a low-lying LUMO, which lies at -3.94 eV relative to vacuum. Incorporation of the ring-fused monomer unit also lowered the overall torsional strain in the polymer backbone (relative to polyisoindigo), and the polymer was successfully used in prototype unipolar n-channel organic thin-film transistors.
Source: openalex_inverted_index · Quality: baseline

Research context

OpenAlex topics: Organic Electronics and Photovoltaics · Synthesis and properties of polymers · Synthesis and pharmacology of benzodiazepine derivatives

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada

Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN), University of Waterloo, 200 University Avenue West, Waterloo, Ontario N2L 3G1, Canada

Stanford Synchrotron Radiation Lightsource, SLAC National Accelerator Laboratory, Menlo Park, California 94025, United States

Funding

Canada Research Chairs · University of Saskatchewan · Natural Sciences and Engineering Research Council of Canada

References (32)

Show source-provided references
1. 10.1039/b914956m10.1039/b914956m ↗
2. 10.1002/adma.20080321110.1002/adma.200803211 ↗
3. 10.1021/ja400881n10.1021/ja400881n ↗
4. 10.1038/nature1385410.1038/nature13854 ↗
5. 10.1039/b812502n10.1039/b812502n ↗
6. 10.1039/C4CS00227J10.1039/C4CS00227J ↗
7. 10.1039/C7TC01680H10.1039/C7TC01680H ↗
8. 10.1039/b909902f10.1039/b909902f ↗
9. 10.1021/cm049391x10.1021/cm049391x ↗
10. 10.1002/adma.20080354110.1002/adma.200803541 ↗
11. 10.1039/C7TC05145J10.1039/C7TC05145J ↗
12. 10.1002/adma.20120179510.1002/adma.201201795 ↗
13. 10.1002/adma.20130494510.1002/adma.201304945 ↗
14. 10.1039/C3PY01598J10.1039/C3PY01598J ↗
15. 10.1002/adma.20130598110.1002/adma.201305981 ↗
16. 10.1002/adma.20160054110.1002/adma.201600541 ↗
17. 10.1039/c3ee40556g10.1039/c3ee40556g ↗
18. 10.1021/acs.chemrev.6b0049810.1021/acs.chemrev.6b00498 ↗
19. 10.1039/C7PY00484B10.1039/C7PY00484B ↗
20. 10.1038/s41467-018-02852-610.1038/s41467-018-02852-6 ↗
21. 10.1039/C5TA07511D10.1039/C5TA07511D ↗
22. 10.1021/acs.macromol.6b0000410.1021/acs.macromol.6b00004 ↗
23. 10.1002/anie.20180051210.1002/anie.201800512 ↗
24. 10.1039/C9TC02021G10.1039/C9TC02021G ↗
25. 10.1021/ma201270610.1021/ma2012706 ↗
26. Frisch, M. J.; Trucks, G.; W. Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision E.01; Gaussian, Inc.: Wallingford, CT, 2013.
27. 10.1107/S002188981200403710.1107/S0021889812004037 ↗
28. 10.1021/acs.chemmater.7b0006710.1021/acs.chemmater.7b00067 ↗
29. 10.1021/ol902512x10.1021/ol902512x ↗
30. 10.1021/acs.chemmater.8b0253510.1021/acs.chemmater.8b02535 ↗
31. 10.1002/adma.20100455410.1002/adma.201004554 ↗
32. 10.1021/cr990257j10.1021/cr990257j ↗