CuAAC reaction pillar arenes

We synthesized various functionalized pillar[5]arenes by the CuAAC reaction between decaall nes 3.21 and azides (Scheme 3.4). Reactions of the clickahle decaalkyne 3.21 with hoylazide, henzylazide, phenylazide and pyrenylazide afforded functionalized pillar[5]arenes with 10 hexyl (3.32), henzyl (3.33), phenyl" (3.34) and pyrenyl moieties (3.35), respectively. Zhao et al. reported hiocompatihle pillar[5]arenes with amphiphilic oligoethylene glycol chains (3.36 and 3.37) hy a CuAAC reaction between 3.21 and... 

Scheme 3.4 Synthesis of per-functionalized pillar[5]arenes from per-ethylated pillar[5]arene via CuAAC reaction.

Penta-functionalized pillar[5]arenes can be prepared from non-symmetrical monomers with reactive moieties (Scheme 3.19). Huang et al. synthesized a pillar[5]arene with five allq nes on the same rim (3.116). A CuAAC reaction between 3.116 and a naphthalene containing an azide... 

Li and co-workers synthesized H5.28 by a CuAAC reaction between a pil-lar[5]arene containing 10 allqme moieties and phenyl azide (Figure 5.27). The K values of the complexes between five diaminoalkane guests and H5.28 were all in the vicinity of 10 (Table 5.7, runs 125-129), which is much larger than that observed for per-methylated pillar[5]arene... 

K<10 M ). Additional hydrogen bonding, such as CH-N, NH-N, and CH/ 7t interactions, caused by introducing phenyl substituents using a CuAAC reaction, improved the host-guest ability compared with simple per-allqrl-ated pillar[5]arenes. 

Huang et al. reported apseudo[l]catenane produced by a combination of pillar[5]arene and crown ether host-guest chemistry. A novel co-pillar[5]-arene, bearing two benzo-18-crown-6 units (8.48), was synthesized by a CuAAC reaction (Figure 8.8). 1,8-Diaminooctane was added as the guest molecule to thread into the pillar[5]arene cavity to form the... 

Wang et al. reported the preparation of a pillar[5]arene bearing two bromide moieties on the same unit by the co-cyclization of 1,4-bis(2-bromoethoxy)benzene with 1,4-dimethoxybenzene [31]. In a similar manner to the decabromide, the mono- and dibromides where readily functionalized by cationization, etherification and CuAAC reactions. 

Scheme 3.13 S nithesis of A1/A2 di-functionalized pillar[5]arene with two different functional groups by co-cyclization, CuAAC and cationic reactions.

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