2,2 -Diamino-1,1 -binaphthalene

Intrinsically microporous Pis have been prepared from 2,2 -diamino-l,l -binaphthalene or 4,4 -(9-fluorenylidene)dianiline. As anhydrides pyromel-litic dianhydride, 3,3, 4,4 -biphenyltetracarboxylic dianhydride, 4,4 -oxydiphthalic anhydride, and 4,4 -(hexafluoroisopropylidene)diphthalic anhydride were used [81]. 

In addition to the dibenzodioxin reaction, the more classical polymerization reaction of imide formation has been used to form PIMs. Weber and co-workers [117, 118] firstly reported the synthesis of soluble poly(amide) and poly(imide) using monomers derived from 9,9 -spirobifluorene. Such a spirobifluorene generates a 90° kink per repeating imit and thus prevoits space-efficient chain packing, resulting in microporous materials with high surface areas. For example, by reacting 2,2 -diamino-9,9 -spirobifluorene (Fig. 5.15, Al) with pyromellitic dianhydride (PMDA) (Fig. 5.15, Bl), a soluble polymer with a BET surface area of 551 m g was obtained [118]. Binaphthalene-based polyimide was synthesized by Ritter et al. 

These types of chiral Schiff bases can be obtained by the condensation of 2,2 -diamino-l,l -binaphthalene with saUcyl aldehydes. 1,2-Diaminocyclohexane can be also used as base material (13). In addition, methods for polymerization and copolymerization of lactic acid compounds have been reported by Hiltunen in a series of papers (14 16). 

An MlP-catalyzed ene reaction between a diketone and an alkene was used to further investigate this phenomenon. The most easily accessible binding sites of an MIP-containing chiral phosphine platinum complexes were poisoned by using diamine derivatives of binaphthol (i.e., 2,2 -diamino-l,l -binaphthalene BINAM) to block access to the substrate (Scheme 20)." ... 

Fig. 2 The chromatograms of enantioseparation using (/ )-MA, iV-trimethyl-2-aminobutanol-bis(trifluoromethanesulfon)imidate CIL 5 as chiral selector, (a) propranolol in HPCE, 10 mmol/L CIL 5 voltage, 16 kV, with anodic detection at 254 nm (b) enantioseparation of 2,2 -diamino-l,r-binaphthalene in HPLC eluent H2O-CH3CN (6 4, v/v) containing 10 mmol/L of chiral selector 5, detection, 254 nm (c) enantioseparation of citronellain GC on 5, split ratio 80 1, FID. Adapted from [76]...

It was found that the CIL, (/ )-A/,A/,N-trimethyl-2-aminobutanol-bis (trifluo-romethanesulfonyl)imide (5), was a good chiral selector that can be used in HPLC for enantioseparation of compounds such as alcohol, amine, and amino acids. The presence of this CIL in the mobile phase led to the enantioseparation of 2,2 -diamino-l,r-binaphthalene (Fig. 2B) [76]. Clearly, these limited studies using CILs in HPLC suggest that more CILs with multiple functional groups need to be explored for enantioseparation of various chiral molecules in HPLC. 

In 1996, Denmark introduced chiral phosphoramide 1, which could be readily synthesized from the parent commercially available (R)-2,2 -diamino-l,l-binaphthalene, as an effective catalyst for the aldol reaction of the preformed trichlorosilyl enol ether of methyl acetate with aldehydes under mild conditions (Scheme 7.1) (2). 

In 2006, Ishihara showed that a diammonium salt of commercially available chiral (S)-2,2 -diamino-l,l -binaphthalene (20) and bis(trifluoromethane)sulfon-... 

Diamino-1,1 -binaphthalene-3,3 -disulfonic acid, D-00052 4,4 -Diamino-3,3 -dibromobiphenyl, D-00068... 

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