Abstract
A novel banana-shaped molecule using 2,8-Dimethyl-6H,12H-5,11-methanodibenzo [b,f] [1,5]diazocine (Tröger’s base) as bent-core was synthesized via double Carbon-Carbon cross-coupling reaction. The double Sonogashira cross-coupling reaction was optimized by using Pd(PPh3)2Cl2 as catalyst, CuI as cocatalyst and diisopropylamine as base in place of triethylamine. The structure of this compound was confirmed by 1H-NMR, 13C-NMR, Fourier transform infrared (FT-IR) spectroscopy and mass spectrometry.
Highlights
Molecules bearing bent-cores have attracted extensive worldwide attention due to their outstanding properties
Banana-shaped molecules with bent-cores and flexible tails can exhibit a variety of novel characteristics involving chirality, polarity, and liquid crystalline (LC) features [8,9,10,11,12]
As shown in Scheme 2, starting from 4-bromoaniline 1, rac-(±)-Tröger’s base 2 was synthesized by condensation of 1 with paraformaldehyde in trifluoroacetic acid (TFA) according to the procedure described in Scheme 1
Summary
Molecules bearing bent-cores have attracted extensive worldwide attention due to their outstanding properties. Some of these molecules have potential applications in asymmetric catalysis [1,2], and others have been wildly used in molecular recognition [3,4,5,6]. Banana-shaped molecules have rigid Λ shape, which will induce intermolecular polarity Because of their special structure, the molecules can pack closely and align in the direction of bending [7]. When bent-core is constructed in the liquid crystal molecules, this special bent shape promotes molecules packed in polar [3] and tilted [13] ways to form chiral lamellar phases such as the B2 and B7 [14,15,16]
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