DataVXACS Applied Materials & InterfacesPaper
journal article·2019-01-09

Charge Carrier Polarity Modulation in Diketopyrrolopyrrole-Based Low Band Gap Semiconductors by Terminal Functionalization

Samrat Ghosh, Reshma Raveendran, Akinori Saeki, Shu Seki, Manoj Namboothiry, Ayyappanpillai Ajayaghosh

ACS Applied Materials & Interfaces· Volume 11· Issue 1
Publisher page
Source abstract

Abstract

Organic semiconductors with variable charge carrier polarity are required for optoelectronic applications. Herein, we report the synthesis of three novel diketopyrrolopyrrole (DPP)-based D–A molecules having three different terminal groups (amide, ester, and dicyano) and study their electronic properties. An increase in electron acceptor strength from amide to dicyano leads to a bathochromic shift in absorption. Photoconductivity and field effect transistor (FET) measurements confirmed that a small increase in acceptor strength can result in a large change in the charge transport properties from p-type to n-type. The molecule with an amide group, DPP–amide, exhibited a moderate p-type mobility (1.3 × 10–2 cm2 V–1 s–1), whereas good n-type mobilities were observed for molecules with an ester moiety, DPP–ester (1.5 × 10–2 cm2 V–1 s–1), and with a dicyano group, DPP–DCV (1 × 10–2 cm2 V–1 s–1). The terminal functional group modification approach presented here is a simple and efficient method to alter the charge carrier polarity of organic semiconductors.
Source: openalex_inverted_index · Quality: baseline

Research context

Electronic materials

OpenAlex topics: Organic Electronics and Photovoltaics · Molecular Junctions and Nanostructures · Conducting polymers and applications

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

Affiliations

Photosciences and Photonics Section, Chemical Sciences and Technology Division, CSIR−National Institute for Interdisciplinary Science and Technology (CSIR−NIIST), Thiruvananthapuram 695019, India

Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST Campus, Thiruvananthapuram 695019, India

School of Physics, Indian Institute of Science Education and Research-Thiruvananthapuram (IISER-TVM), Thiruvananthapuram 695551, India

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan

Funding

Council of Scientific and Industrial Research · Science and Engineering Research Board · Department of Science and Technology, Ministry of Science and Technology · Ministry of Human Resource Development

References (62)

Show source-provided references
1. 10.1039/c3cs60127g10.1039/c3cs60127g ↗
2. 10.1002/adma.20130434610.1002/adma.201304346 ↗
3. 10.1021/cr100380z10.1021/cr100380z ↗
4. 10.1002/anie.20070192010.1002/anie.200701920 ↗
5. 10.1021/ja400881n10.1021/ja400881n ↗
6. 10.1039/c2cs15313k10.1039/c2cs15313k ↗
7. 10.1021/ja207364310.1021/ja2073643 ↗
8. 10.1002/adma.20120179510.1002/adma.201201795 ↗
9. 10.1016/s1369-7021(07)70017-210.1016/s1369-7021(07)70017-2 ↗
10. 10.1039/c1cc10321k10.1039/c1cc10321k ↗
11. 10.1002/adma.20130508410.1002/adma.201305084 ↗
12. 10.1021/cm402106310.1021/cm4021063 ↗
13. 10.1002/adma.20090362810.1002/adma.200903628 ↗
14. 10.1002/adfm.20110182010.1002/adfm.201101820 ↗
15. 10.1002/adma.20110200710.1002/adma.201102007 ↗
16. 10.1039/c7tc01680h10.1039/c7tc01680h ↗
17. 10.1021/cm047863210.1021/cm0478632 ↗
18. 10.1039/c4cp01700e10.1039/c4cp01700e ↗
19. 10.1021/acs.chemmater.6b0192910.1021/acs.chemmater.6b01929 ↗
20. 10.1002/adma.20160383010.1002/adma.201603830 ↗
21. 10.1002/aelm.20170010010.1002/aelm.201700100 ↗
22. 10.1021/acs.macromol.5b0122510.1021/acs.macromol.5b01225 ↗
23. 10.1039/c7sc04665k10.1039/c7sc04665k ↗
24. 10.1021/cm202852f10.1021/cm202852f ↗
25. 10.1002/adma.20170574510.1002/adma.201705745 ↗
26. 10.1002/adma.20160505310.1002/adma.201605053 ↗
27. 10.1021/jacs.8b0214410.1021/jacs.8b02144 ↗
28. 10.1021/acs.chemmater.8b0367010.1021/acs.chemmater.8b03670 ↗
29. 10.1002/anie.20110620310.1002/anie.201106203 ↗
30. 10.1021/acsami.5b0807810.1021/acsami.5b08078 ↗
31. 10.1021/jo200311710.1021/jo2003117 ↗
32. 10.1002/adma.20170378310.1002/adma.201703783 ↗
33. 10.1039/c2cc17886a10.1039/c2cc17886a ↗
34. 10.1021/jp806830510.1021/jp8068305 ↗
35. 10.1002/adom.20140055910.1002/adom.201400559 ↗
36. 10.1002/adma.20160001310.1002/adma.201600013 ↗
37. 10.1038/s41598-017-00277-710.1038/s41598-017-00277-7 ↗
38. 10.1021/acs.accounts.5b0033410.1021/acs.accounts.5b00334 ↗
39. 10.1002/adfm.20110182010.1002/adfm.201101820 ↗
40. 10.1039/c6tc00687f10.1039/c6tc00687f ↗
41. 10.1021/acsami.6b0696710.1021/acsami.6b06967 ↗
42. 10.1021/acs.macromol.6b0095410.1021/acs.macromol.6b00954 ↗
43. 10.1021/jacs.5b0973710.1021/jacs.5b09737 ↗
44. 10.1002/adfm.20120094010.1002/adfm.201200940 ↗
45. 10.1021/acsami.7b0170210.1021/acsami.7b01702 ↗
46. 10.1002/asia.20140008910.1002/asia.201400089 ↗
47. 10.1002/adma.20130598110.1002/adma.201305981 ↗
48. 10.1002/adfm.20120306510.1002/adfm.201203065 ↗
49. 10.1002/adma.20120536110.1002/adma.201205361 ↗
50. 10.1021/ja107678m10.1021/ja107678m ↗
51. 10.1021/cr00002a00410.1021/cr00002a004 ↗
52. 10.1039/c7cc05883g10.1039/c7cc05883g ↗
53. 10.1002/adma.20060150010.1002/adma.200601500 ↗
54. 10.1021/cm503915t10.1021/cm503915t ↗
55. 10.1002/anie.20100230710.1002/anie.201002307 ↗
56. 10.1021/sc500561710.1021/sc5005617 ↗
57. 10.1039/c3mh00098b10.1039/c3mh00098b ↗
58. 10.1021/ma202778p10.1021/ma202778p ↗
59. 10.1039/c4cp00473f10.1039/c4cp00473f ↗
60. 10.1021/ja103685j10.1021/ja103685j ↗
61. 10.1002/adma.20160540810.1002/adma.201605408 ↗
62. 10.1038/ncomms501310.1038/ncomms5013 ↗