Macrocycles for Host-Guest Chemistry

Host-compounds recognize and incorporate specific molecules, atoms or ions (guests) into the molecules to form complexes. In the formation of these complexes, a variety of forces such as electrostatic interaction, hydrophobic interaction, hydrogen bonding, etc. are utilized to create high selectivity. Molecular sensors, synthetic enzymes, separation systems, etc. utilize the high guest selectivity of these host compounds. Synthesis of new host compounds with even higher selectivity are currently being developed.
For example, Shinkai and co-workers have developed exciting purification techniques for fullerene C60 employing calixarene. According to these techniques, the stirring of crude fullerene and tert-butylcalix[8]arene in toluene causes only C60 to be incorporated in the calixarene to form and precipitate a complex. Filtration and subsequent stirring of the complex in chloroform cause it to decompose to yield C60 of high purity as a precipitate. This method has been reported to be an efficient purification technique in obtaining C60 compared with conventional column purification techniques.

Crown Ethers

Calixarenes

Cyclophanes

Cyclodextrins

Crown Ethers

A1603 A1603 A1604 A1604 A1568 A1568
A1404 A1404 A1323 A1323 A1324 A1324
A1552 A1552 B1154 B1154 B1249 B1249
B1539 B1539 B2245 B2245 B2181 B2181
B2189 B2189 C1713 C1713 C1714 C1714
C1942 C1942 C1943 C1943 C0858 C0858
C0859 C0859 C0860 C0860 C1736 C1736
D2323 D2323 D2743 D2743 D2744 D2744
D1533 D1533 D1830 D1830 D2684 D2684
D2877 D2877 D2878 D2878 D2321 D2321
D1668 D1668 F0448 F0448 F0451 F0451
H1070 H1070 H1215 H1215 H0932 H0932
H0982 H0982 H0983 H0983 H0990 H0990
M1489 M1489 N0561 N0561 N0562 N0562
P1143 P1143 T1874 T1874 T1875 T1875
T1426 T1426 T1691 T1691 T1597 T1597
T2540 T2540 T1959 T1959 T1876 T1876
T1878 T1878 T1600 T1600 T2642 T2642
T2541 T2541 T1879 T1879 T1972 T1972
A1603 4'-Acetylbenzo-15-crown 5-Ether
A1604 4'-Acetylbenzo-18-crown 6-Ether
A1568 2-(Allyloxymethyl)-18-crown 6-Ether
A1404 4'-Aminobenzo-15-crown 5-Ether
A1323 1-Aza-15-crown 5-Ether
A1324 1-Aza-18-crown 6-Ether
A1552 1-Aza-12-crown 4-Ether
B1154 Benzo-15-crown 5-Ether
B1249 Benzo-12-crown 4-Ether
B1539 Benzo-18-crown 6-Ether
B2245 Bis(1,4-phenylene)-34-crown 10-Ether
B2181 4'-Bromobenzo-18-crown 6-Ether
B2189 4'-Bromobenzo-15-crown 5-Ether
C1713 4'-Carboxybenzo-15-crown 5-Ether
C1714 4'-Carboxybenzo-18-crown 6-Ether
C1942 15-Crown-4 [4-(2,4-Dinitrophenylazo)phenol]
C1943 18-Crown-5 [4-(2,4-Dinitrophenylazo)phenol]
C0858 12-Crown 4-Ether
C0859 15-Crown 5-Ether
C0860 18-Crown 6-Ether
C1736 24-Crown 8-Ether
D2323 4,13-Diaza-18-crown 6-Ether
D2743 4,10-Diaza-12-crown 4-Ether
D2744 4,10-Diaza-15-crown 5-Ether
D1533 Dibenzo-18-crown 6-Ether
D1830 Dibenzo-24-crown 8-Ether
D2684 Dibenzo-30-crown 10-Ether
D2877 Dibenzo-15-crown 5-Ether
D2878 Dibenzo-21-crown 7-Ether
D2321 N,N'-Dibenzyl-4,13-diaza-18-crown 6-Ether
D1668 Dicyclohexano-18-crown 6-Ether
F0448 4'-Formylbenzo-15-crown 5-Ether
F0451 4'-Formylbenzo-18-crown 6-Ether
H1070 1,4,7,10,13,16-Hexaazacyclooctadecane
H1215 1,4,7,10,13,16-Hexaazacyclooctadecane Hexahydrochloride
H0932 4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane
H0982 2-(Hydroxymethyl)-12-crown 4-Ether
H0983 2-(Hydroxymethyl)-15-crown 5-Ether
H0990 2-(Hydroxymethyl)-18-crown 6-Ether
M1489 4'-Methoxycarbonylbenzo-15-crown 5-Ether
N0561 4'-Nitrobenzo-15-crown 5-Ether
N0562 4'-Nitrobenzo-18-crown 6-Ether
P1143 N-Phenylaza-15-crown 5-Ether
T1874 1,4,7,10-Tetraazacyclododecane
T1875 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic Acid
T1426 1,4,7,10-Tetraazacyclododecane Tetrahydrochloride
T1691 1,4,8,12-Tetraazacyclopentadecane
T1597 1,4,8,11-Tetraazacyclotetradecane
T2540 Tetraethyl 1,4,8,11-Tetraazacyclotetradecane-1,4,8,11-tetraacetate
T1959 1,4,8,11-Tetrathiacyclotetradecane
T1876 1,5,9-Triazacyclododecane
T1878 1,4,7-Triazacyclononane
T1600 1,4,7-Triazacyclononane Trihydrochloride
T2642 Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetate
T2541 Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate
T1879 1,4,7-Trimethyl-1,4,7-triazacyclononane (stabilized with NaHCO3)
T1972 1,4,7-Trithiacyclononane
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Calixarenes

B1750 B1750 B1809 B1809 B2221 B2221
H0714 H0714 C1435 C1435 C1455 C1455
H0713 H0713 H0889 H0889 S0469 S0469
S0470 S0470 S0471 S0471 T2563 T2563
U0069 U0069
B1750 4-tert-Butylcalix[8]arene
B1809 4-tert-Butylcalix[4]arene
B2221 4-tert-Butylcalix[5]arene
H0714 4-tert-Butylcalix[6]arene (contains 5-10% Benzene)
C1435 Calix[8]arene
C1455 Calix[4]arene (contains ca. 8% Chloroform)
H0713 Calix[6]arene
H0889 4-Methyl-1-acetoxycalixarene [mixture of [6] and [8]] (contains 5-10% Acetone)
S0469 4-Sulfocalix[4]arene Hydrate
S0470 4-Sulfocalix[6]arene Hydrate
S0471 4-Sulfocalix[8]arene Hydrate
T2563 Tetraethyl 4-tert-Butylcalix[4]arene-O,O',O'',O'''-tetraacetate
U0069 C-Undecylcalix[4]resorcinarene Monohydrate
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Cyclophanes

C1749 C1749 D2210 D2210 P1165 P1165
T1378 T1378
C1749 Cyclobis(paraquat-1,4-phenylene) Tetrakis(hexafluorophosphate)
D2210 2,11-Dithia[3.3]paracyclophane
P1165 [2.2]Paracyclophane
T1378 1,6,20,25-Tetraaza[6.1.6.1]paracyclophane
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Cyclodextrins

A1916 A1916 A2122 A2122 A2123 A2123
B3026 B3026 C0776 C0776 C0777 C0777
C0869 C0869 C0900 C0900 G0263 G0263
H0979 H0979 M1219 M1219 M1356 M1356
D1732 D1732 M1212 M1212 M1876 M1876
M1381 M1381 M1644 M1644 M1645 M1645
M1741 M1741 M1956 M1956 M1957 M1957
P0977 P0977 T2452 T2452 T2451 T2451
T1844 T1844 T1094 T1094 T2450 T2450
A1916 3A-Amino-3A-deoxy-(2AS,3AS)-beta-cyclodextrin Hydrate
A2122 3A-Amino-3A-deoxy-(2AS,3AS)-alpha-cyclodextrin Hydrate
A2123 3A-Amino-3A-deoxy-(2AS,3AS)-gamma-cyclodextrin Hydrate
B3026 2,2-Bis[4-(per-O-methyl-alpha-cyclodextrin-6-yloxy)phenyl]propane
C0776 alpha-Cyclodextrin
C0777 beta-Cyclodextrin
C0869 gamma-Cyclodextrin
C0900 beta-Cyclodextrin
G0263 6-O-alpha-D-Glucosyl-beta-cyclodextrin
H0979 Hydroxypropyl-beta-cyclodextrin
M1219 6-O-alpha-D-Maltosyl-beta-cyclodextrin
M1356 Methyl-beta-cyclodextrin (mixture of several Methylated)
D1732 Methyl-beta-cyclodextrin (2,6-Di-O-methyl- and partially 2,3,6-Tri-O-methyl- mixture)
M1212 Mono-6-O-mesitylenesulfonyl-gamma-cyclodextrin
M1876 Mono-6-O-(2-naphthyl)-per-O-methyl-alpha-cyclodextrin
M1381 Mono-6-O-(p-toluenesulfonyl)-beta-cyclodextrin
M1644 Mono-6-O-(p-toluenesulfonyl)-alpha-cyclodextrin
M1645 Mono-6-O-(p-toluenesulfonyl)-gamma-cyclodextrin
M1741 Mono-2-O-(p-toluenesulfonyl)-beta-cyclodextrin
M1956 Mono-2-O-(p-toluenesulfonyl)-alpha-cyclodextrin
M1957 Mono-2-O-(p-toluenesulfonyl)-gamma-cyclodextrin
P0977 Poly-beta-cyclodextrin (Cross-linked by Epichlorohydrin)
T2452 5,10,15,20-Tetrakis[3,5-bis(per-O-methyl-alpha-cyclodextrin-6-yloxy)phenyl]-21H,23H-porphine
T2451 5,10,15,20-Tetrakis[4-(per-O-methyl-alpha-cyclodextrin-6-yloxy)phenyl]-21H,23H-porphine
T1844 Triacetyl-beta-cyclodextrin
T1094 Trimethyl-beta-cyclodextrin
T2450 1,1,1-Tris[4-(per-O-methyl-alpha-cyclodextrin-6-yloxy)phenyl]ethane
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Literature

1) Calixarene
A. Ikeda, S. Shinkai, Chem. Rev., 1997, 97, 1713 [DOI]; M. Ayabe, S. Shinkai, TCIMAIL, 2003, number 118, 2 [DOI].
2) Cyclodextrin
K. Takahashi, Chem. Rev., 1998, 98, 2013 [DOI].
3) Thiacalixarene
N. Morohashi, S. Miyano, TCIMAIL, 2004, number 122, 2 [DOI].

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