o-Carborane functionalized pentacenes: synthesis, molecular packing and ambipolar organic thin-film transistors

o-Carborane functionalized pentacenes: synthesis, molecular packing and ambipolar organic thin-film transistors

New 6,13-bis[1'-(C≡C)-2'-R-1',2'-C2B10H10]pentacenes (R = H, Me, Et, n-Bu) are synthesized and fully characterized. The results show that the alkyl substituents on the second cage carbon have a significant impact on the molecular packing, and the incorporation of the o-carboranyl...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2015-08, Vol.51 (60), p.12004-12007
Hauptverfasser: Guo, Jixi, Liu, Danqing, Zhang, Jiahui, Zhang, Jiji, Miao, Qian, Xie, Zuowei
Format: Artikel
Sprache:eng
Schlagworte:
Cage
Carbon
Converting
Energy levels
Molecular orbitals
P-type semiconductors
Semiconductor devices
Synthesis
Thin films
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Beschreibung
Zusammenfassung:New 6,13-bis[1'-(C≡C)-2'-R-1',2'-C2B10H10]pentacenes (R = H, Me, Et, n-Bu) are synthesized and fully characterized. The results show that the alkyl substituents on the second cage carbon have a significant impact on the molecular packing, and the incorporation of the o-carboranyl moiety into a π conjugated system can lower both LUMO and HOMO energy levels, converting a typical p-type semiconductor into an ambipolar one.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc03608a