Complexation of Triptycene-Based Cylindrical Macrotricyclic Polyether toward Diquaternary Salts:  Ion-Controlled Binding and Release of the Guests

Abstract

Triptycene-based cylindrical macrotricyclic polyether 1 has been proved to be an efficient host for the complexation with diquaternary salts in solution and in the solid state. Moreover, it was also found that binding and release of the guest molecules could be easily controlled by the addition and removal of potassium ions.

Synthesis and host-guest properties of pillar[6]arenes

“…The results showed that the overall yield and the ratio 2 6 /2 5 increased with increasing the chain length of alkoxy, which implied that a long chain linked to hydropuinone was helpful to form pillar [6]arenes. The isolated yields of pillar [6] arenes 2 6 af were around 30%50% (Table 3), significantly improved from the previous results [8,9].…”

“…Recently, the para-bridged analogues, named pillararenes 2 n , have also been reported ( Figure 1) [712]. For example, Ogoshi reported the BF 3 catalyzed condensation of 1,4-dimethoxybenzene and paraformaldehyde [7] 2 5 for the synthesis of pillar [5]arene 2 5 with 5-member rings. Pillar [5]arenes 2 5 are a new class of macrocyclic hosts, and have attracted considerable attention because of their applications in host-guest chemistry [713].…”

“…For example, Ogoshi reported the BF 3 catalyzed condensation of 1,4-dimethoxybenzene and paraformaldehyde [7] 2 5 for the synthesis of pillar [5]arene 2 5 with 5-member rings. Pillar [5]arenes 2 5 are a new class of macrocyclic hosts, and have attracted considerable attention because of their applications in host-guest chemistry [713]. Previously we reported the synthesis of the first pillar [6]arenes 2 6 which contained 6-member rings via the p-toluenesulfonic acid catalyzed condensation reaction of 2,5-bis(benzyloxymethyl)-1,4-dialkoxybenzene [8].…”

“…Previously we reported the synthesis of the first pillar [6]arenes 2 6 which contained 6-member rings via the p-toluenesulfonic acid catalyzed condensation reaction of 2,5-bis(benzyloxymethyl)-1,4-dialkoxybenzene [8]. Although 2 5 were obtained in good yield, the yields of 2 6 were very low (< 11%) [8,9].…”

Synthesis of Fréchet-type dendritic homotriptycenes

“…Triptycene and its derivatives play an important role in materials science [1][2][3][4][5][6][7][8][9] because of their rigid 3D structure [10][11][12] , unique electrochemical and photochemical properties [13][14][15][16][17] , potential biological activities and pharmaceutical properties [18][19][20] , and applications in supramolecular chemistry [21][22][23][24][25][26][27][28] . However, only few reports about homotriptycenes have been described [29][30][31] .…”