Abstract
Published data about the synthesis and complexing properties of calix[4]pyrroles towards anions, ion pairs and neutral molecules of various nature are analyzed, summarized and classified. Synthetic approaches to the parent macrocycles and methods of their functionalization are presented. General principles, mechanisms and driving forces of the formation of calix[4]pyrrole-based supramolecular complexes are disscussed. Most attention is concentrated on the factors providing effective control of the formation of such structure.
The bibliography includes 79 references.
References
1.
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. ,
1956
3.
Sessler J.L., Anzenbacher P., Jursíková K., Miyaji H., Genge J.W., Tvermoes N.A., Allen W.E., Shriver J.A., Gale P.A., Král V.
Pure and Applied Chemistry ,
1998
4.
Sessler J.L., Anzenbacher, P., Miyaji H., Jursíková K., Bleasdale E.R., Gale P.A.
Industrial & Engineering Chemistry Research ,
2000
5.
Gale P.
Coordination Chemistry Reviews ,
2000
6.
Gale P.A., Anzenbacher Jr. P., Sessler J.L.
Coordination Chemistry Reviews ,
2001
7.
Gale P.A., García-Garrido S.E., Garric J.
Chemical Society Reviews ,
2008
8.
Caltagirone C., Gale P.A.
Chemical Society Reviews ,
2009
9.
10.
Ballester P.
Israel Journal of Chemistry ,
2011
11.
Rothemund P., Gage C.L.
Journal of the American Chemical Society ,
1955
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1950
13.
Brown W.H., Hutchinson B.J., MacKinnon M.H.
Canadian Journal of Chemistry ,
1971
14.
Jacoby D., Isoz S., Floriani C., Chiesi-Villa A., Rizzoli C.
Journal of the American Chemical Society ,
1995
15.
De Angelis S., Solari E., Floriani C., Chiesi-Villa A., Rizzoli C.
Journal of the American Chemical Society ,
1994
16.
De Angelis S., Solari E., Floriani C., Chiesi-Villa A., Rizzoli C.
Journal of the American Chemical Society ,
1994
17.
Blas J.R., Márquez M., Sessler J.L., Luque F.J., Orozco M.
Journal of the American Chemical Society ,
2002
18.
Wu Y., Wang D., Sessler J.L.
Journal of Organic Chemistry ,
2001
19.
Sessler J.L., Pavel Anzenbacher, Jr., *, Shriver J.A., Jursíková K., Lynch V.M., Marquez M.
Journal of the American Chemical Society ,
2000
20.
Levitskaia T.G., Marquez M., Sessler J.L., Shriver J.A., Vercouter T., Moyer B.A.
Chemical Communications ,
2003
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1958
22.
Anzenbacher, P., Jursíková K., Lynch V.M., Gale P.A., Sessler J.L.
Journal of the American Chemical Society ,
1999
23.
Bonomo L., Solari E., Toraman G., Scopelliti R., Floriani C., Latronico M.
Chemical Communications ,
1999
24.
Camiolo S., Gale P.A.
Chemical Communications ,
2000
25.
Woods C.J., Camiolo S., Light M.E., Coles S.J., Hursthouse M.B., King M.A., Gale P.A., Essex J.W.
Journal of the American Chemical Society ,
2002
26.
Sessler J.L., Andrievsky A., Gale P.A., Lynch V.
1996
27.
Sessler J.L., Král V., Shishkanova T.V., Gale P.A.
Proceedings of the National Academy of Sciences of the United States of America ,
2002
28.
10.1002/(SICI)1521-3773(19981002)37:18<2475::AID-ANIE2475>3.0.CO;2-7
29.
Lee C., Miyaji H., Yoon D., Sessler J.L.
Chemical Communications ,
2008
30.
Lee C., Na H., Yoon D., Won D., Cho W., Lynch V.M., Shevchuk S.V., Sessler J.L.
Journal of the American Chemical Society ,
2003
31.
Miyaji H., Kim H., Sim E., Lee C., Cho W., Sessler J.L., Lee C.
Journal of the American Chemical Society ,
2005
32.
Lee C., Lee J., Na H., Yoon D., Miyaji H., Cho W., Sessler J.L.
Journal of Organic Chemistry ,
2005
33.
Gale P.A., Sessler J.L., Lynch V., Sansom P.I.
Tetrahedron Letters ,
1996
34.
Panda P.K., Lee C.
Organic Letters ,
2004
35.
Panda P.K., Lee C.
Journal of Organic Chemistry ,
2005
36.
Furusho Y., Kawasaki H., Nakanishi S., Aida T., Takata T.
Tetrahedron Letters ,
1998
37.
Anzenbacher, P., Jursíková K., Shriver J.A., Miyaji H., Lynch V.M., Sessler J.L., Gale P.A.
Journal of Organic Chemistry ,
2000
38.
Miyaji H., Anzenbacher Jr P., Sessler J.L., Bleasdale E.R., Gale P.A.
Chemical Communications ,
1999
39.
Miyaji H., Sato W., Sessler J.L., Lynch V.M.
Tetrahedron Letters ,
2000
40.
Sato W., Miyaji H., Sessler J.L.
Tetrahedron Letters ,
2000
41.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1950
42.
Kulikova O.M., Mamardashvili N.Z.
Russian Journal of Organic Chemistry ,
2010
43.
Pognon G., Mamardashvilli N.Z., Weiss J.
Tetrahedron Letters ,
2007
44.
45.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1955
46.
Dietrich B., Fyles D.L., Fyles T.M., Lehn J.
Helvetica Chimica Acta ,
1979
47.
Bauer V.J., Clive D.L., Dolphin D., Paine J.B., Harris F.L., King M.M., Loder J., Wang S.W., Woodward R.B.
Journal of the American Chemical Society ,
1983
48.
Peschke W., Schiessl P., Schmidtchen F.P., Bissinger P., Schier A.
Journal of Organic Chemistry ,
1995
49.
Atwood J.L., Holman K.T., Steed J.W.
Chemical Communications ,
1996
50.
Schmidtchen F.P., Berger M.
Chemical Reviews ,
1997
51.
Staffilani M., Hancock K.S., Steed J.W., Holman K.T., Atwood J.L., Juneja R.K., Burkhalter R.S.
Journal of the American Chemical Society ,
1997
52.
Antonisse M.M., Reinhoudt D.N.
Chemical Communications ,
1998
53.
Sessler J.L., Davis J.M., Král V., Kimbrough T., Lynch V.
Organic and Biomolecular Chemistry ,
2003
54.
Gale P.A.
Coordination Chemistry Reviews ,
2001
55.
56.
Gale P.A., Sessler J.L., Král V., Lynch V.
Journal of the American Chemical Society ,
1996
57.
Allen W.E., Gale P.A., Brown C.T., Lynch V.M., Sessler J.L.
Journal of the American Chemical Society ,
1996
58.
Gale P.A., Sessler J.L., Allen W.E., Tvermoes N.A., Lynch V.
Chemical Communications ,
1997
59.
Furusho Y., Aida T.
Chemical Communications ,
1997
60.
Phenylurea-Equipped p-tert-Butylthiacalix[4]Arenes as the Synthetic Receptors for Monocharged Anions
Galukhin Andrei Vladimirovich, Shabalin Konstantin Vasil'evich, Antipin Igor' Sergeevich, Konovalov Aleksandr Ivanovich, Stoikov Ivan Ivanovich
Mendeleev Communications ,
2013
61.
Danil de Namor A.F., Khalife R.
Physical Chemistry Chemical Physics ,
2010
62.
Mamardashvili G.M., Mamardashvili N.Z., Koifman O.I.
Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya ,
2011
63.
64
Chem. Zentr. II ,
1931
64.
Koifman O.I., Mamardashvili N.Z.
Russian Chemical Bulletin ,
2013
65.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1950
66.
Fowler C.J., Haverlock T.J., Moyer B.A., Shriver J.A., Gross D.E., Marquez M., Sessler J.L., Hossain M.A., Bowman-James K.
Journal of the American Chemical Society ,
2008
67.
Moyer B.A., Sloop F.V., Fowler C.J., Haverlock T.J., Kang H., Delmau L.H., Bau D.M., Hossain M.A., Bowman-James K., Shriver J.A., Bill N.L., Gross D.E., Marquez M., Lynch V.M., Sessler J.L., et. al.
Supramolecular Chemistry ,
2010
68.
Shinkai S., Ogawa T., Nakaji T., Kusano Y., Nanabe O.
Tetrahedron Letters ,
1979
69.
Shinkai S., Ogawa T., Kusano Y., Manabe O.
Chemistry Letters ,
1980
70.
71.
Mahoney J.M., Nawaratna G.U., Beatty A.M., Duggan P.J., Smith B.D.
Inorganic Chemistry ,
2004
73.
Kirkovits G.J., Shriver J.A., Gale P.A., Sessler J.L.
Journal of Inclusion Phenomena and Macrocyclic Chemistry ,
2001
74.
Tong C.C., Quesada R., Sessler J.L., Gale P.A.
Chemical Communications ,
2008
75.
Sessler J.L., Kim S.K., Gross D.E., Lee C., Kim J.S., Lynch V.M.
Journal of the American Chemical Society ,
2008
76.
Custelcean R., Delmau L.H., Moyer B.A., Sessler J.L., Cho W., Gross D., Bates G.W., Brooks S.J., Light M.E., Gale P.A.
Angewandte Chemie - International Edition ,
2005
77.
Wintergerst M.P., Levitskaia T.G., Moyer B.A., Sessler J.L., Delmau L.H.
Journal of the American Chemical Society ,
2008
78.
79.
Borman C.J., Custelcean R., Hay B.P., Bill N.L., Sessler J.L., Moyer B.A.
Chemical Communications ,
2011
80.
Gross D., Schmidtchen F., Antonius W., Gale P., Lynch V., Sessler J.
Chemistry - A European Journal ,
2008
81.
Caltagirone C., Bill N.L., Gross D.E., Light M.E., Sessler J.L., Gale P.A.
Organic and Biomolecular Chemistry ,
2010