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Luminescent Organic 1D Nanomaterials Based on Bis(β‐diketone)carbazole Derivatives
Author(s) -
Liu Xingliang,
Xu Defang,
Lu Ran,
Li Bin,
Qian Chong,
Xue Pengchong,
Zhang Xiaofei,
Zhou Huipeng
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001858
Subject(s) - stacking , intramolecular force , nanomaterials , nanowire , materials science , van der waals force , nanofiber , side chain , carbazole , molecule , conjugated system , luminescence , nanostructure , polymer , chemical engineering , photochemistry , nanotechnology , chemistry , organic chemistry , optoelectronics , engineering , composite material
A series of new triphenylamine‐functionalized bis(β‐diketone)s bridged by a carbazole (C n BDKC, 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.