Luminescent organic 1D nanomaterials based on Bis(β-diketone)carbazole derivatives

Document Type

Article

Publication Date

2-1-2011

Abstract

A series of new triphenylamine-functionalized bis(β-diketone)s bridged by a carbazole (CnBDKC, n=1, 4, 8, 16) with twisted intramolecular charge-transfer emission in polar solvents has been synthesized. The length of the carbon chains has a significant effect on the self-assembling properties of the compounds. Well-defined 1D nanowires were easily generated from C1BDKC with a methyl group by a reprecipitation approach directed by π-stacking interaction, and the molecules packed into J-aggregates in the nanowires. In addition, 1D nanofibers based on C16BDKC bearing a long hexadecyl chain were prepared through the organogelation process, and H-aggregates were formed driven by the synergistic effect of π-stacking interaction and van der Waals force in the gel phase. C4BDKC and C8BDKC containing butyl and octyl side chains, respectively, cannot arrange into dispersed nanostructures, probably because π-π interaction between conjugated moieties might be disturbed by the interaction between the side chains, which is, however, not strong enough to dominate the self-assembling process. Notably, the nanowires based on C1BDKC and the gel nanofibers from C16BDKC can emit strong green light under irradiation, which suggests that these 1D nanomaterials may have potential applications in emitting materials as well as photonic devices. Given the green light: Well-defined 1D nanowires and nanofibers have been fabricated by reprecipitation and organogelation from triphenylamine-functionalized bis(β-diketone)s bridged by carbazole with alkyl chains of different length (CnBDKC, n=1, 16, respectively; see picture). The nanostructures give strong green fluorescent emission. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Publication Source (Journal or Book title)

Chemistry - A European Journal

First Page

1660

Last Page

1669

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