Abstract
Calixphyrins are hybrid macrocycles that contain both sp2- and sp3-hybridized carbon atoms and hence bear analogy to both porphyrins and calixpyrroles. Due to the presence of sp3-hybridized carbon atoms, π-conjugation is disrupted in calixphyrins, which leads to conformational flexibility. Hence, these molecules find a use in anion binding, host-guest chemistry and metal-coordination chemistry. During the last decade, studies on calixphyrins have been a topic of wide interest to researchers. Various functionalities have been introduced to the structure of calixphyrins, leading to the development of expanded calixphyrins, core-modified calixphyrins and N-confused calixphyrins with diverse applications. This review outlines the detailed historical origin of the synthesis of calixphyrins with emphasis on current research and development in this area. The modular syntheses of normal calixphyrins, expanded calixphyrins, core-modified calixphyrins and N-confused calixphyrins are also discussed, along with their applicative aspects.
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References
Smith KM (ed) (1975) Porphyrins and metalloporphyrins. Elsevier, Amsterdam
Sessler JL, Anzenbacher P Jr, Jursíková K, Miyaji H, Genge JW, Tvermoes NA, Allen WE, Shriver JA, Gale PA, Kral V (1998) Pure Appl Chem 70:2401–2408
Floriani C (1996) Chem Comm 1996:1257–1263
Solari G, Solari E, Lemecier G, Floriani C, Chiesi-Villa A, Rizzoli C (1997) Inorg Chem 36:2691–2695
Crescenzi R, Solari E, Floriani C, Chiesi-Villa A, Rizzoli C (1999) J Am Chem Soc 121:1695–1706
Crescenzi R, Solari E, Floriani C, Re N, Chiesi-Villa A, Rizzoli C (1999) Organometallics 18:606–618
Dolphin D (1970) J Heterocycl Chem 7:275–283
Montforts F-P, Gerlach B, Höper F (1994) Chem Rev 94:327–347
Mauzerall D (1962) J Am Chem Soc 84:2437–2445
Botulinski A, Buchler JW, Wicholas M (1987) Inorg Chem 26:1540–1543
Buchler JW, Lee YJ, Scheidt WR (1988) Inorg Chem 27:927–933
Renner MW, Buchler JW (1995) J Phys Chem 99:8045–8049
Bischoff I, Feng X, Senge MO (2001) Tetrahedron 57:5573–5583
Kral V, Sessler JL, Zimmerman RS, Seidel D, Lynch V, Andrioletti B (2000) Angew Chem Int Ed 39:1055–1058
Bucher C, Seidel D, Lynch V, Kral V, Sessler JL (2000) Org Lett 2:3103–3106
Dehaen W (2010) In: Gale P, Dahaen W (eds) Topics in heterocyclic chemistry, vol 24. Springer, Berlin
Dolensky B, Kroulık J, Kral V, Sessler JL, Dvorakova H, Bour P, Bernatkova M, Bucher C, Lynch V (2004) J Am Chem Soc 126:13714–13722
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
Holaday MGD, Tarafdar G, Kumar A, Reddy MLP, Srinivasan A (2014) Dalton Trans 43:7699–7703
Bucher C, Devillers CH, Moutet JC, Pécaut J, Royal G, Saint-Aman E, Thomas F (2005) Dalton Trans 22:3620–3631
Bernatkova M, Andrioletti B, Kral V, Rose E, Vaissermann J (2004) J Org Chem 69:8140–8143
Battersby AR, Fookes CJR, Matcham GWJ, Donald E (1980) Nature (London) 285:17–21
Lehr PA, Doss M (1981) Dtsch Med Wochenschr 106:241–245
Koch M, Breithaupt C, Kiefersauer R, Freigang J, Huber R, Messerschmidt A (2004) EMBO J 23:1720–1728
Lindsey JS (1999) In: Kadish K, Smith KM, Guilard R (eds) The porphyrin handbook, vol 1. Academic, San Diego
Sratton CW, Mitchell WM (1997) Antimicrob Infect Dis Newsl 16:33–38
Piarulli U, Floriani C, Chiesi-Villa A, Rizzoli C (1994) J Chem Soc Chem Comm 1994: 895–896
Bonomo L, Solari E, Scopelliti R, Latronico M, Floriani C (1999) Chem Comm 1999: 2227–2228
Bonomo L, Solari E, Scopelliti R, Floriani C, Re N (2000) J Am Chem Soc 122:5312–5326
Harmjanz M, Bozidarevic I, Scott MJ (2001) Org Lett 3:2281–2284
Turner B, Botoshansky M, Eichen Y (1998) Angew Chem Int Ed 37:2475–2478
Buchler JA, Puppe L (1974) Liebigs Ann Chem 1974:1046–1062
Solari E, Musso F, Floriani C, Chiesi-Villa A, Rizzoli C (1994) J Chem Soc Dalton Trans 1994:2015–2017
Harmjanz M, Gill HS, Scott MJ (2001) J Org Chem 66:5374–5383
Senge MO, Runge S, Speck M, Senge KR (2000) Tetrahedron 56:8927–8932
Segawa H, Azumi R, Shimidzu T (1992) J Am Chem Soc 114:7564–7565
Setsune J, Wada K, Higashino H (1994) Chem Lett 1994:213–216
Jiang X, Nurco DJ, Smith KM (1996) Chem Comm 1996:1759–1760
Xie H, Smith KM (1992) Tetrahedron Lett 33:1197–1200
Krattinger B, Callot HJ (1998) Tetrahedron Lett 39:1165–1168
Harmjanz M, Gill HS, Scott MJ (2000) J Am Chem Soc 122:10476–10477
Benech J-M, Bonomo L, Solari E, Scopelliti R, Floriani C (1999) Angew Chem Int Ed 38:1957–1959
Khoury RG, Jaquinod L, Nguyen LT, Smith KM (1998) Heterocycles 47:113–119
Wytko JA, Michels M, Zander L, Lex J, Schmickler H, Vogel E (2000) J Org Chem 65:8709–8714
Sessler JL, Gebauer A, Weghorn SJ (1999) In: Kadish K, Smith KM, Guilard R (eds) The porphyrin handbook, vol 2. Academic, San Diego, p 55
Won D-H, Toganoh M, Terada Y, Fukatsu S, Uno H, Furuta H (2008) Angew Chem Int Ed 47:5438–5441
Bucher C, Zimmerman RS, Lynch V, Kral V, Sessler JL (2001) J Am Chem Soc 123:2099–2100
Beyzavi MH, Lentz D, Reissig H-U, Weihe A (2013) Chem Eur J 19:6203–6208
Karthik G, Krushna PV, Srinivasan A, Chandrashekar TK (2013) J Org Chem 78:8496–8501
Ochi N, Nakao Y, Sato H, Matano Y, Imahori H, Sakaki S (2009) J Am Chem Soc 131:10955–10963
Chandrashekar TK, Venkatraman S (2003) Acc Chem Res 36:676–691
Sessler JL, Seidel D (2003) Angew Chem Int Ed 42:5134–5175
Srinivasan A, Furuta H (2005) Acc Chem Res 38:10–20
Chmielewski PJ, Latos-Grażyński L (2005) Coord Chem Rev 249:2510–2533
Stepień L, Latos-Grażyński M (2005) Acc Chem Res 38:88–98
Gupta I, Ravikanth M (2006) Coord Chem Rev 250:468–518
Matano Y, Miyajima T, Nakabuchi T, Imahori H, Ochi N, 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
Matano Y, Miyajima T, Ochi N, Nakao Y, Sakaki S, Imahori H (2008) J Org Chem 73:5139–5142
Stepień M, Latos-Grażyński L, Szterenberg L, Panek J, Latajka Z (2004) J Am Chem Soc 126:4566–4580
Hung C-H, Chang G-F, Kumar A, Lin G-F, Luo L-Y, Ching W-M, Diau EW-G (2008) Chem Commun 8:978–980
Fahrni CJ, O’Halloran TV (1999) J Am Chem Soc 121:11448–11458
Burdette SC, Frederickson CJ, Bu W, Lippard SJ (2003) J Am Chem Soc 125:1778–1787
Chang G-F, Kumar A, Ching W-M, Chu H-W, Hung C-H (2009) Chem Asian J 4:164–173
Skoneiczny J, Latos-Grażyński L, Szterenberg L (2012) Org Biomol Chem 10:3463–3471
Ahmad S, Yadav KK, Bhattacharya S, Chauhan P, Chauhan SMS (2015) J Org Chem 80:3880–3890
Salini PS, Thomas AP, Sabarinathan R, Ramakrishnan S, Sreedevi KCG, Reddy MLP, Srinivasan A (2011) Chem Eur J 17:6598–6601
Ramakrishnan S, Anju KS, Thomas AP, Sreedevi KCG, Salini PS, Holaday MGD, Suresh E, Srinivasan A (2012) Organometallics 31:4166–4173
Ganapathi E, Chattarjee T, Ravikanth M (2015) Dalton Trans 44:2763–2770
Furuta H, Maeda H, Osuka A (2002) Chem Comm 2002:1795–1804
Bohle DS, Chen W-C, Hung C-H (2002) Inorg Chem 41:3334–3336
Chen W-C, Hung C-H (2001) Inorg Chem 40:5070–5071
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 6:398–401
Ishida M, Omagari T, Hirosawa R, Jono K, Sung YM, Yasutake Y, Uno H, Toganoh M, Nakanotani H, Fukatsu S, Kim D, Furuta H (2016) Angew Chem Int Ed 55:12045–12049
Albrett AM, Thomas KE, Maslek S, Mlodzianowska A, Conradie J, Beavers CM, Ghosh A, Brothers PJ (2014) Inorg Chem 53:5486–5493
Tay ACY, Frogley BJ, Ware DC, Brothers PJ (2018) Dalton Trans 47:3388–3399
Prieto JB, Arbeloa FL, Martinez VM, Lopez TA, Arbeloa IL (2004) J Phys Chem A 108:5503–5508
Pushpanandan P, Maurya YK, Omagari T, Hirosawa R, Ishida M, Mori S, Yasutake Y, Fukatsu S, Mack J, Nyokong T, Furuta H (2017) Inorg Chem 56:12572–12580
Salini PS, Anju KS, Reddy MLP, Srinivasan A (2013) Chem Commun 49:5769–5771
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The author acknowledges Council of Scientific and Industrial Research (CSIR), New Delhi, India for financial support during this research work.
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Singhal, A. Functional Calixphyrins: Synthetic Strategies and Applications. Top Curr Chem (Z) 376, 21 (2018). https://doi.org/10.1007/s41061-018-0199-y
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DOI: https://doi.org/10.1007/s41061-018-0199-y