journal article·2024-01-12Open access

Solubilizing Benzodifuranone-Based Conjugated Copolymers with Single-Oxygen-Containing Branched Side Chains

Diego R. Hinojosa, Nathan J. Pataki, Pietro Rossi, Andreas Erhardt, Shubhradip Guchait, Francesca Pallini, Christopher McNeill, Christian Müller, Mario Caironi, Michael Sommer

ACS Applied Polymer Materials· Volume 6· Issue 1

Abstract

Single-oxygen-containing branched side chains are designed and used to solubilize n-type copolymers consisting of BDF (benzodifuranone), isatin, and thiophene-based units. We present a simple synthetic approach to side chains with varying linker distances between the backbone and the branching point. The synthetic pathway is straightforward and modular and starts with commercially available reagents. The side chains give rise to excellent solubilities of BDF-thiophene copolymers of up to 90 mg/mL, while still being moderate in size (26-34 atoms large). The excellent solubility furthermore allows high molar mass materials. BDF-thiophene copolymers are characterized in terms of optoelectronic and thermoelectric properties. The electrical conductivity of chemically doped polymers is found to scale with molar mass, reaching ∼1 S/cm for the highest molar mass and longest backbone-branching point distance.
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Research context

OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Perovskite Materials and Applications

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

Affiliations

Institut für Chemie, Technische Universität Chemnitz, Straße der Nationen 62, 09111 Chemnitz, Germany

Forschungszentrum MAIN, TU Chemnitz, Rosenbergstraße 6, 09126 Chemnitz, Germany

Center for Nano Science and Technology, Via Rubattino 81, 20134 Milano, Italy

Department of Physics, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133Milano ,Italy

Department of Materials Science and Engineering, Monash University, Clayton, Victoria 3800, Australia

Institute Charles Sadron, Université de Strasbourg, Strasbourg F-67000, France

Department of Materials Science, Università di Milano-Bicocca, via Cozzi 55, 20125 Milan, Italy

Department of Chemistry and Chemical Engineering Chalmers University of Technology Göteborg 412 96, Sweden

Funding

H2020 Marie Sklodowska-Curie Actions

References (54)

Show source-provided references
1. 10.1002/cplu.20200032510.1002/cplu.202000325 ↗
2. 10.1021/ja00155a00710.1021/ja00155a007 ↗
3. 10.1021/cm402080510.1021/cm4020805 ↗
4. 10.1002/anie.20080545610.1002/anie.200805456 ↗
5. 10.1002/adma.20040096310.1002/adma.200400963 ↗
6. 10.1039/C8PY01221K10.1039/C8PY01221K ↗
7. 10.1038/nmat259410.1038/nmat2594 ↗
8. 10.1021/ma802839a10.1021/ma802839a ↗
9. 10.1021/ma101771t10.1021/ma101771t ↗
10. 10.1021/ma300075x10.1021/ma300075x ↗
11. 10.1021/ja061664x10.1021/ja061664x ↗
12. 10.1021/ma00193a03910.1021/ma00193a039 ↗
13. 10.1021/ja972373e10.1021/ja972373e ↗
14. 10.1021/am303138q10.1021/am303138q ↗
15. 10.1038/nphoton.2009.19210.1038/nphoton.2009.192 ↗
16. 10.1021/ja303204m10.1021/ja303204m ↗
17. 10.1021/ja068771b10.1021/ja068771b ↗
18. 10.1021/ma070900110.1021/ma0709001 ↗
19. 10.1021/ma902566h10.1021/ma902566h ↗
20. 10.1039/C8PY00820E10.1039/C8PY00820E ↗
21. 10.1039/C4CP02322F10.1039/C4CP02322F ↗
22. 10.1039/D0CC04967K10.1039/D0CC04967K ↗
23. 10.1002/adma.20120179510.1002/adma.201201795 ↗
24. 10.1039/C3TC31755B10.1039/C3TC31755B ↗
25. 10.1002/adfm.20130423110.1002/adfm.201304231 ↗
26. 10.1002/adma.20120268910.1002/adma.201202689 ↗
27. 10.1126/sciadv.adf349510.1126/sciadv.adf3495 ↗
28. 10.1021/acs.chemmater.8b0273910.1021/acs.chemmater.8b02739 ↗
29. 10.1007/s11743-001-0185-110.1007/s11743-001-0185-1 ↗
30. 10.1021/ja00078a01210.1021/ja00078a012 ↗
31. 10.1021/ja805407g10.1021/ja805407g ↗
32. 10.1021/jacs.5b1323310.1021/jacs.5b13233 ↗
33. 10.1016/j.giant.2021.10006410.1016/j.giant.2021.100064 ↗
34. 10.1038/s41586-022-05295-810.1038/s41586-022-05295-8 ↗
35. 10.1021/jacs.2c1305110.1021/jacs.2c13051 ↗
36. 10.1021/jacs.5b0094510.1021/jacs.5b00945 ↗
37. 10.1021/ja412533d10.1021/ja412533d ↗
38. 10.1039/C6SC01380E10.1039/C6SC01380E ↗
39. 10.1039/C6PY01922F10.1039/C6PY01922F ↗
40. 10.1021/ja300318310.1021/ja3003183 ↗
41. 10.1021/ja403624a10.1021/ja403624a ↗
42. 10.1002/adfm.20140182210.1002/adfm.201401822 ↗
43. 10.1002/pol.2021049310.1002/pol.20210493 ↗
44. 10.1039/C5PY00782H10.1039/C5PY00782H ↗
45. 10.1002/adfm.20200044910.1002/adfm.202000449 ↗
46. 10.1038/nature1385410.1038/nature13854 ↗
47. 10.1021/acsapm.1c0151110.1021/acsapm.1c01511 ↗
48. 10.1002/aelm.20170058110.1002/aelm.201700581 ↗
49. 10.1021/acsaem.8b0077710.1021/acsaem.8b00777 ↗
50. 10.1063/1.492688510.1063/1.4926885 ↗
51. 10.1038/s41563-021-01008-010.1038/s41563-021-01008-0 ↗
52. 10.1038/natrevmats.2016.5010.1038/natrevmats.2016.50 ↗
53. 10.1002/anie.20220022110.1002/anie.202200221 ↗
54. 10.1107/S002188981302774X10.1107/S002188981302774X ↗