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Helical Stacking Tuned by Alkoxy Side Chains in π‐Conjugated Triphenylbenzene Discotic Derivatives
Author(s) -
Bao Chunyan,
Lu Ran,
Jin Ming,
Xue Pengchong,
Tan Changhui,
Xu Tinghua,
Liu Guofa,
Zhao Yingying
Publication year - 2006
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.200501058
Subject(s) - alkoxy group , stacking , conjugated system , absorption (acoustics) , side chain , transmission electron microscopy , crystallography , absorption spectroscopy , materials science , toluene , molecule , hydrogen bond , chemistry , phase (matter) , polymer , photochemistry , polymer chemistry , organic chemistry , alkyl , nanotechnology , composite material , optics , physics
We report on the synthesis and self‐assembly of a new series of discotic molecules containing triphenylbenzene as the core and alkoxy side chain with varying length. It was found that compounds 3 a – c , 4 b and 5 b could form stable gels in several apolar solvents. Transmission electron microscopy (TEM) images revealed that their morphologies were very different for the different alkoxy‐substituted organogels. In toluene or hexane, 3 b and 3 c resulted in both left‐ and right‐handed helical fibers, whereas 3 a resulted in straight rigid fibers; 4 b and 5 b resulted in most straight fibers with a few twisted fibers. The results from FT‐IR and UV/Vis absorption spectroscopy indicated that the hydrogen bonding and π–π interactions were the main driving forces for the formation of the self‐assembled gels. Further detailed analysis of their aggregation modes were conducted by UV‐visible absorption spectra and X‐ray diffraction (XRD) measurements. Based on these findings, the influence of these peripheral alkoxy substituents on the gel formation and the aggregation mode were discussed. The special enhanced fluorescent emissions, which resulted from aggregation, were also found in the gel phase.