Abstract
This chapter covers advances in calix[n]phyrin chemistry since 2001, focusing on their synthesis and properties as anion complexants. Over the last 8 years, the structural variety of calixphyrins has significantly increased, and several applications as anion complexants were reported.
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Abbreviations
- DDQ:
-
4,5-Dichloro-3,6-dioxo-1,2-benzonitrile
- NCP:
-
N-confused porphyrin
- NMR:
-
Nuclear magnetic resonance
- OEP:
-
β-Octaethylporphyrin
- PTSA:
-
4-Methylphenylsulphonic acid
- PVC:
-
Poly(vinyl chloride)
- TBA:
-
Tetrabutylammonium
- TFA:
-
Trifluoroacetic acid
- TPP:
-
meso-Tetraphenylporphyrin
References
Sessler JL, Zimmerman RS, Bucher C, Král V, Andrioletti B (2001) Pure Appl Chem 73:1041–1057
Bischoff I, Feng X, Senge MO (2001) Tetrahedron 57:5573–5583
Senge MO, Kalisch WW, Bischoff I (2000) Chem Eur J 6:2721–2738
Senge MO, Runge S, Speck M, Ruhlandt-Senge K (2000) Tetrahedron 56:8927–8932
Sergeeva NN, Senge MO (2006) Tetrahedron Lett 47:6169–6172
Sergeeva NN, Shaker YM, Finnigan EM, McCabe T, Senge MO (2007) Tetrahedron 63:12454–12464
Senge MO, Bischoff I (2001) Eur J Org Chem:1735–1751
Kalisch WW, Senge MO (1998) Angew Chem Int Ed 37:1107–1109
Senge MO (2005) Acc Chem Res 38:733–743
Krattinger B, Callot HJ (1996) Tetrahedron Lett 37:7699–7702
Krattinger B, Callot HJ (1998) Tetrahedron Lett 39:1165–1168
Krattinger B, Callot HJ (1999) Eur J Org Chem:1857–1867
LeSaulnier TD, Graham BW, Geier GR (2005) Tetrahedron Lett 46:5633–5637
Kojima T, Hanabusa K, Ohkubo K, Shiro M, Fukuzumi S (2008) Chem Commun:6513–6515
Milgrom LR (1983) Tetrahedron 39:3895–3898
Milgrom LR, Mofidi N, Jones CC, Harriman A (1989) J Chem Soc Perkin Trans 2:301–309
Milgrom LR, Nolan KB, Povey DC (1989) Chem Commun:1751–1753
Milgrom LR, Hill JP, Dempsey PF (1994) Tetrahedron 37:13477–13484
Milgrom LR, Hill JP, Yahioglu G (1995) J Heterocycl Chem 32:97–101
Dolušić E, Toppet S, Smeets S, Van Meervelt L, Tinant B, Dehaen W (2003) Tetrahedron 59:395–400
Hill JP, Hewitt IJ, Anson CE, Powell AL, McCarty PA, Karr PA, Zandler ME, D’Souza F (2004) J Org Chem 69:5861–5869
Hill JP, Schmitt W, McCarty AL, Ariga K, D’Souza F (2005) Eur J Org Chem:2893–2902
Hill JP, Schumacher AL, D’Souza F, Labuta J, Redshaw C, Elsegood MRJ, Aoyagi M, Nakanishi T, Ariga K (2006) Inorg Chem 45:8288–8296
Hill JP, Sandanayaka ASD, McCarty AL, Karr PA, Zandler ME, Charvet R, Ariga K, Araki Y, Ito O, D’Souza F (2006) Eur J Org Chem:595–603
Schumacher AL, Sandanayaka ASD, Hill JP, Ariga K, Karr PA, Araki Y, Ito O, D’Souza F (2007) Chem Eur J 13:4628–4635
Schumacher AL, Hill JP, Ariga K, D’Souza F (2007) Electrochem Commun 9:2751–2754
Xie Y, Hill JP, Schumacher AL, Sandanayaka ASD, Araki Y, Karr PA, Labuta J, D’Souza F, Ito O, Anson CE, Powell AK, Ariga K (2008) J Phys Chem C 112:10559–10572
D’Souza F, Subbaiyan NK, Xie Y, Hill JP, Ariga K, Ohkubo K, Fukuzumi S (2009) J Am Chem Soc 134:16138–16146
Da Silva C, Bonomo L, Solari E, Scopelliti R, Floriani C, Re N (2000) Chem Eur J 6:4518–4531
Bonomo L, Solari E, Scopelliti R, Floriani C, Re N (2000) J Am Chem Soc 122:5312–5326
Re N, Bonomo L, Da Silva C, Solari E, Scopelliti R, Floriani C (2001) Chem Eur J 7:2536–2546
Floriani C, Floriani-Moro R (2000) Porphyrin handbook, vol 3, pp 405–420
Král V, Sessler JL, Zimmerman RS, Seidel D, Lynch V, Andrioletti B (2000) Angew Chem Int Ed 39:1055–1058
Dolenský B, Kroulik J, Král V, Sessler JL, Dvořáková H, Bouř P, Bernátkova M, Bucher C, Lynch V (2004) J Am Chem Soc 126:13714–13722
Bucher C, Seidel D, Lynch V, Král V, Sessler JL (2000) Org Lett 2:3103–3106
Alešković M, Halasz I, Basarić N, Mlinarić-Majerski K (2009) Tetrahedron 65:2051–2058
Harmjanz M, Scott MJ (2000) Chem Commun:397–398
Harmjanz M, Gill HS, Scott MJ (2001) J Org Chem 66:5374–5383
Harmjanz M, Božidarević I, Scott MJ (2001) Org Lett 3:2281–2284
Harmjanz M, Gill HS, Scott MJ (2000) J Am Chem Soc 122:10476–10477
Gill HS, Harmjanz M, Santamaria J, Finger I, Scott MJ (2004) Angew Chem Int Ed 43:485–490
Bernátkova M, Andrioletti B, Král V, Rose E, Vaissermann J (2004) J Org Chem 69:8140–8143
Bernátkova M, Dvořáková H, Andrioletti B, Král V, Bouř P (2005) J Phys Chem A 109:5518–5526
Orlewska C, Toppet S, Dehaen W (2005) Synth Commun 35:1953–1959
Bucher C, Devillers CH, Moutet J-C, Pécaut J, Royal G, Saint-Aman E, Thomas F (2005) Dalton Trans:3620–3631
Jha SC, Lorch M, Lewis RA, Archibald SJ, Boyle RW (2007) Org Biomol Chem 5:1970–1974
Orlewska C, Maes W, Toppet S, Dehaen W (2005) Tetrahedron Lett 46:6067–6070
O’Brien AY, McGann JP, Geier GR (2007) J Org Chem 72:4084–4092
Sharada DS, Muresan AZ, Muthukumaran K, Lindsey JS (2005) J Org Chem 70:3500–3510
Gryko DT, Koszarna B (2005) Eur J Org Chem:3314–3318
Huong NTT, KlÃmková P, Sorrenti A, Mancini G, DraÅ¡ar P (2009) Steroids 74:715–720
Bucher C, Zimmerman RS, Lynch V, Král V, Sessler JL (2001) J Am Chem Soc 123:2099–2100 (Erratum ibid. 123:12744)
Chen W, Liu TJ (2008) Chinese Chem Lett 19:1199–1201
Bucher C, Zimmerman RS, Lynch V, Sessler JL (2003) Chem Commun:1646–1647
Ka J-W, Lee C-H (2001) Tetrahedron Lett 42:4527–4529
Inoue M, Ikeda C, Kawata Y, Venkatraman S, Furukuwa K, Osuka A (2007) Angew Chem Int Ed 46:2306–2309
Shimizu S, Aratani N, Osuka A (2006) Chem Eur J 12:4909–4918
Li X, Chmielewski P, Xiang J, Xu J, Jiang L, Li Y, Liu H, Zhu D (2006) Org Lett 8:1137–1140
Li X, Chmielewski P, Xiang J, Xu J, Jiang L, Li Y, Liu H, Zhu D (2006) J Org Chem 71:9739–9742
Hung C-H, Liaw C-C, Chin M-W, Chang G-F, Chuang C-H (2006) J Porphyr Phthalocyan 10:953–961
Furuta H, Ishizuka T, Osuka A, Uwatoko Y, Ishikawa Y (2001) Angew Chem Int Ed 40:2323–2325
Furuta H, Ishizuka T, Osuka A (2003) Inorg Chem Commun:398–401
Won DH, Toganoh M, Terada Y, Fukatsu S, Uno H, Furuta H (2008) Angew Chem Int Ed 47:5438–5441
Stępień M, Latos-Grażynski L, Szterenberg L, Panek J, Latajka Z (2004) J Am Chem Soc 126:4566–4580
Hung C-H, Chang G-F, Kumar A, Lin GF, Luo L-Y, Chin W-M, Diau EW-G (2008) Chem Commun:978–980
Colby DA, Lash TD (2002) J Org Chem 67:1031–1033
Lash TD, El-Beck JA, Dolby DA (2009) J Org Chem 74:8830–8833
Gupta I, Fröhlich R, Ravikanth M (2006) Chem Commun:3726–3728
Gupta I, Fröhlich R, Ravikanth M (2008) Eur J Org Chem:1884–1900
Matano Y, Miyajima T, Ochi N, Nakao Y, Sakaki S, Imahori H (2008) J Org Chem 73:5139–5142
Gokulnath S, Chandrashekar TK (2008) Org Lett 10:637–640
Matano Y, Miyajima T, Nakabuchi T, Imahori H, Ochi N, Nakao Y, Sakaki S (2006) J Am Chem Soc 128:11760–11761
Matano Y, Miyajima T, Ochi N, Nakabuchi T, Shiro M, Nakao Y, Sakaki S, Imahori H (2008) J Am Chem Soc 130:990–1002 (Erratum ibid. 130:14123)
Ochi N, Nakao Y, Sato H, Matano Y, Imahori H, Sakaki S (2009) J Am Chem Soc 131:10955–10963
Matano Y, Fujita M, Miyajima T, Imahori H (2009) Organometallics 28:6213–6217
Matano Y, Imahori H (2009) Acc Chem Res 42:1193–1204
Sessler JL, An D, Cho W-S, Lynch V (2003) Angew Chem Int Ed 42:2278–2281
Sessler JL, An D, Cho W-S, Lynch V, Marquez M (2005) Chem Commun:540–542
Setsune J, Tsukajima A, Watanabe J (2007) Tetrahedron Lett 48:1531–1535
Anand VG, Saito S, Shimizu S, Osuka A (2005) Angew Chem Int Ed 44:7244–7248
Rhee SW, Na YH, Do Y, Youngkyu K, Kim J (2000) Inorg Chim Acta 309:49–56
Bucher C, Devillers CH, Moutet J-C, Royal G, Saint-Aman E (2004) New J Chem 28:1584–1587
Ka J-W, Won DH, Lee C-H (2003) Bull Korean Chem Soc 24:661–663
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Dehaen, W. (2010). Calix[n]phyrins: Synthesis and Anion Recognition. In: Gale, P., Dehaen, W. (eds) Anion Recognition in Supramolecular Chemistry. Topics in Heterocyclic Chemistry, vol 24. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_51
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