Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors
Here, we design and synthesize three new diketopyrrolopyrrole (DPP) derivatives with naphthalene, possessing large-scaled p-delocalized electronic structure, as the flanking groups and both linear (n-decyl and n-dodecyl) and branched (2-hexyldecyl)alkyl chains as substitutions as active layer for hi...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Journal Article |
| Published: |
Royal Society of Chemistry
2018
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| Online Access: | http://hdl.handle.net/20.500.11937/69666 |
| _version_ | 1848762101562081280 |
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| author | Liu, Q. Sun, H. Blaikie, C. Caporale, C. Manzhos, S. Feron, K. Macleod, J. Massi, Massimiliano Bottle, S. Bell, J. Noh, Y. Sonar, P. |
| author_facet | Liu, Q. Sun, H. Blaikie, C. Caporale, C. Manzhos, S. Feron, K. Macleod, J. Massi, Massimiliano Bottle, S. Bell, J. Noh, Y. Sonar, P. |
| author_sort | Liu, Q. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | Here, we design and synthesize three new diketopyrrolopyrrole (DPP) derivatives with naphthalene, possessing large-scaled p-delocalized electronic structure, as the flanking groups and both linear (n-decyl and n-dodecyl) and branched (2-hexyldecyl)alkyl chains as substitutions as active layer for high performance organic field-effect transistors (OFETs). The thermal, photophysical properties, energy levels and solid state molecular stacking have been studied in detail. All the materials show excellent thermal stability with a decomposition temperature of 400 °C, high semi-crystallinity feature, suitable HOMO & LUMO energy levels, and varying crystalline domain sizes in thin films. Bottom-contact/top-gate transistor devices are thus fabricated to investigate the mobility. Encouragingly, all compounds function well in OFET devices and show significant potential as p-type semiconducting materials. The monomer with the n-decyl alkyl chain (D-DPPN) shows the highest mobility of 0.019 cm2V-1s-1, with the Ion/Ioffratio reaching 106. We for the first time synthesize naphthalene flanked DPP monomers and achieve high mobility in OFET devices when using these monomers without any further functionalization as semiconductors directly. The primary result that high mobility is observed for monomers only opens a new way for further DPP application and provides more possibilities for constructing high performance polymeric and small molecular semiconductors based on this new DPP dye. |
| first_indexed | 2025-11-14T10:42:13Z |
| format | Journal Article |
| id | curtin-20.500.11937-69666 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T10:42:13Z |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-696662019-06-17T01:10:32Z Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors Liu, Q. Sun, H. Blaikie, C. Caporale, C. Manzhos, S. Feron, K. Macleod, J. Massi, Massimiliano Bottle, S. Bell, J. Noh, Y. Sonar, P. Here, we design and synthesize three new diketopyrrolopyrrole (DPP) derivatives with naphthalene, possessing large-scaled p-delocalized electronic structure, as the flanking groups and both linear (n-decyl and n-dodecyl) and branched (2-hexyldecyl)alkyl chains as substitutions as active layer for high performance organic field-effect transistors (OFETs). The thermal, photophysical properties, energy levels and solid state molecular stacking have been studied in detail. All the materials show excellent thermal stability with a decomposition temperature of 400 °C, high semi-crystallinity feature, suitable HOMO & LUMO energy levels, and varying crystalline domain sizes in thin films. Bottom-contact/top-gate transistor devices are thus fabricated to investigate the mobility. Encouragingly, all compounds function well in OFET devices and show significant potential as p-type semiconducting materials. The monomer with the n-decyl alkyl chain (D-DPPN) shows the highest mobility of 0.019 cm2V-1s-1, with the Ion/Ioffratio reaching 106. We for the first time synthesize naphthalene flanked DPP monomers and achieve high mobility in OFET devices when using these monomers without any further functionalization as semiconductors directly. The primary result that high mobility is observed for monomers only opens a new way for further DPP application and provides more possibilities for constructing high performance polymeric and small molecular semiconductors based on this new DPP dye. 2018 Journal Article http://hdl.handle.net/20.500.11937/69666 10.1039/c8nj01453a Royal Society of Chemistry fulltext |
| spellingShingle | Liu, Q. Sun, H. Blaikie, C. Caporale, C. Manzhos, S. Feron, K. Macleod, J. Massi, Massimiliano Bottle, S. Bell, J. Noh, Y. Sonar, P. Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors |
| title | Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors |
| title_full | Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors |
| title_fullStr | Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors |
| title_full_unstemmed | Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors |
| title_short | Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors |
| title_sort | naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors |
| url | http://hdl.handle.net/20.500.11937/69666 |