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Pure Appl. Chem., 1998, Vol. 70, No. 12, pp. 2401-2408

http://dx.doi.org/10.1351/pac199870122401

Functionalized calix[4]pyrroles

J. L. Sessler, P. Anzenbacher, Jr., K. Jursíková, H. Miyaji, J. W. Genge, N. A. Tvermoes, W. E. Allen, J. A. Shriver, P. A. Gale and V. Král

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  • Bhatt Keyur D., Makwana Bharat A., Vyas Disha J., Mishra Divya R., Jain Vinod K.: Selective recognition by novel calix system: ICT based chemosensor for metal ions. Journal of Luminescence 2014, 146, 450. <http://dx.doi.org/10.1016/j.jlumin.2013.10.004>
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  • Ghosh Sudip Kumar, Ishida Masatoshi, Li Jiazhu, Cha Won-Young, Lynch Vincent M., Kim Dongho, Sessler Jonathan L.: Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole. Chem. Commun. 2014, 50, 3753. <http://dx.doi.org/10.1039/c4cc00686k>
  • Chandra Brijesh, Mahanta Sanjeev P., Pati Narendra N., Baskaran Sambath, Kanaparthi Ravi K., Sivasankar Chinnappan, Panda Pradeepta K.: Calix[2]bispyrrolylarenes: New Expanded Calix[4]pyrroles for Fluorometric Sensing of Anions via Extended π-Conjugation. Org. Lett. 2013, 15, 306. <http://dx.doi.org/10.1021/ol3032158>
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  • Aydogan Abdullah, Akar Ahmet: Tri- and Pentacalix[4]pyrroles: Synthesis, Characterization and Their Use in the Extraction of Halide Salts. Chemistry A European Journal 2012, 18, 1999. <http://dx.doi.org/10.1002/chem.201101605>
  • Mahanta Sanjeev P., Kumar B. Sathish, Baskaran Sambath, Sivasankar Chinnappan, Panda Pradeepta K.: Colorimetric Sensing of Fluoride Ion by New Expanded Calix[4]pyrrole through Anion−π Interaction. Org Lett 2012, 14, 548. <http://dx.doi.org/10.1021/ol203165x>
  • Park Ja-Young, Skonieczny Kamil, Aratani Naoki, Osuka Atsuhiro, Gryko Daniel T., Lee Chang-Hee: Calix[4]pyrroles bearing proximally meso–meso linking straps: synthesis and anion binding properties. Chem. Commun. 2012, 48, 8060. <http://dx.doi.org/10.1039/c2cc33537a>
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  • Sessler Jonathan L., Anzenbacher Pavel Jr., Jursikova Karolina, Miyaji Hidekazu, Genge John W., Tvermoes Nicolai A., Allen William E., Shriver James A., Gale Philip A., Kral Vladimir: ChemInform Abstract: Functionalized Calix[4]pyrroles. ChemInform 2010, 30, no. <http://dx.doi.org/10.1002/chin.199939269>
  • Su Xun-Cheng, Zhu Shou-Rong, Lin Hua-Kuan, Chen Yun-Ti: Studies on the Novel Calix [4] pyrrole and Its High Selectivity for p-Nitrophenol. Chin J Chem 2010, 19, 705. <http://dx.doi.org/10.1002/cjoc.20010190714>
  • Farinha Andreia S.F., Tomé Augusto C., Cavaleiro José A.S.: Synthesis of new calix[4]pyrrole derivatives via 1,3-dipolar cycloadditions. Tetrahedron 2010, 66, 7595. <http://dx.doi.org/10.1016/j.tet.2010.07.024>
  • Lee Gon-Ann, Wang Wen-Chieh, Shieh Minghuey, Kuo Ting-Shen: A novel synthesis of calix[4]thiophenes and calix[4]furans. Chem Commun 2010, 46, 5009. <http://dx.doi.org/10.1039/c0cc00437e>
  • Jain Vinod K., Mandalia Hiren C.: Azocalix[4]pyrroles: one-pot microwave and one drop water assisted synthesis, spectroscopic characterization and preliminary investigation of its complexation with copper (II). J Incl Phenom Macrocycl Chem 2009, 63, 27. <http://dx.doi.org/10.1007/s10847-008-9485-6>
  • Alešković Marija, Halasz Ivan, Basarić Nikola, Mlinarić-Majerski Kata: Synthesis, structural characterization, and anion binding ability of sterically congested adamantane-calix[4]pyrroles and adamantane-calixphyrins. Tetrahedron 2009, 65, 2051. <http://dx.doi.org/10.1016/j.tet.2009.01.007>
  • Mahanta Sanjeev P., Panda Pradeepta K.: Unusual ring annulation during condensation of acetylacetone with pyrrole. Tetrahetron Lett 2009, 50, 890. <http://dx.doi.org/10.1016/j.tetlet.2008.12.033>
  • Chauhan Shive Murat Singh, Garg Bhaskar, Bisht Tanuja: Synthesis and anion binding of 2-arylazo-meso-octamethylcalix[4]pyrroles. Supramol Chem 2009, 21, 394. <http://dx.doi.org/10.1080/10610270802061192>
  • Aydogan A., Sessler J. L., Akar A., Lynch V.: Calix[4]pyrroles with Long Alkyl Chains: Synthesis, Characterization, and Anion Binding Studies. Supramol Chem 2008, 20, 11. <http://dx.doi.org/10.1080/10610270701429789>
  • Electrochemical and 19F NMR Detection of Anions, Ion-pairs, and a Zwitterionic Amino Acid with a Ferrocene-based Hetero-ditopic Receptor Bearing o-(Carboxamido)trifluoroacetophenone and Crown-ether Ligands. Bulletin of the Korean Chemical Society 2008, 29, 2355. <http://dx.doi.org/10.5012/bkcs.2008.29.12.2355>
  • Miyaji Hidekazu, Hong Seong-Jin, Jeong Seung-Doo, Yoon Dae-Wi, Na Hee-Kyung, Hong Jooyeon, Ham Sihyun, Sessler Jonathan L., Lee Chang-Hee: A Binol-Strapped Calix[4]pyrrole as a Model Chirogenic Receptor for the Enantioselective Recognition of Carboxylate Anions. Angew Chem 2007, 119, 2560. <http://dx.doi.org/10.1002/ange.200604161>
  • Miyaji Hidekazu, Hong Seong-Jin, Jeong Seung-Doo, Yoon Dae-Wi, Na Hee-Kyung, Hong Jooyeon, Ham Sihyun, Sessler Jonathan L., Lee Chang-Hee: A Binol-Strapped Calix[4]pyrrole as a Model Chirogenic Receptor for the Enantioselective Recognition of Carboxylate Anions. Angew Chem Int Ed 2007, 46, 2508. <http://dx.doi.org/10.1002/anie.200604161>
  • Dehaen Wim, Gale Philip A., Garc?a-Garrido Sergio E., Kostermans Maarten, Light Mark E.: Anion recognition by N-confused calix[4]pyrrole-?-carbaldehyde and its Knoevenagel reaction derivatives. New J Chem 2007, 31, 691. <http://dx.doi.org/10.1039/b616467f>
  • Pfeffer Frederick M., Lim Kieren F., Sedgwick Kathryn J.: Indole as a scaffold for anion recognition. Org Biomol Chem 2007, 5, 1795. <http://dx.doi.org/10.1039/b702804k>
  • Bates Gareth W., Gale Philip A., Light Mark E.: Isophthalamides and 2,6-dicarboxamidopyridines with pendant indole groups: a ?twisted? binding mode for selective fluoride recognition. Chem Commun 2007, 2121. <http://dx.doi.org/10.1039/b703905k>
  • Liu Jianhui, Muth Enrico, Flörke Ulrich, Henkel Gerald, Merz Klaus, Sauvageau Janelle, Schwake Erik, Dyker Gerald: Alkylation of Arenes with Benzylic and Propargylic Alcohols – Classicalversus Fancy Catalysts. Adv Synth Catal 2006, 348, 456. <http://dx.doi.org/10.1002/adsc.200505411>
  • Valente Artur J.M., Sobral Abílio J.F.N., Jiménez Alfonso, Patachia Sílvia, Oliveira Ana R.C.B., Lobo Victor M.M.: Effect of different electrolytes on the swelling properties of calyx[4]pyrrole-containing polyacrylamide membranes. Euro Poly J 2006, 42, 2059. <http://dx.doi.org/10.1016/j.eurpolymj.2006.04.002>
  • Dey Soumen, Pal Kuntal, Sarkar Sabyasachi: An efficient and eco-friendly protocol to synthesize calix[4]pyrroles. Tetrahetron Lett 2006, 47, 5851. <http://dx.doi.org/10.1016/j.tetlet.2006.06.085>
  • Cafeo Grazia, Kaledkowski Andrzej, Kohnke Franz H., Messina Angela: Strapped Calix[2]furan[4]pyrroles, Novel Examples of Ditopic Molecular Receptors. Supramol Chem 2006, 18, 273. <http://dx.doi.org/10.1080/10610270500484811>
  • Ji Xue Kui, Black David StC., Colbran Stephen B., Craig Donald C., Edbey Khaled M., Harper Jason B., Willett Gary D.: meso-Indanyl calix[4]pyrrole receptors. Tetrahedron 2005, 61, 10705. <http://dx.doi.org/10.1016/j.tet.2005.08.082>
  • Gu Rong, Depraetere Stefaan, Kotek Jan, Budka Jan, Wagner-Wysiecka Ewa, Biernat Jan F., Dehaen Wim: Anion recognition by α-arylazo-N-confused calix[4]pyrroles. Org Biomol Chem 2005, 3, 2921. <http://dx.doi.org/10.1039/b507508d>
  • Novel Synthesis of Phlorin Derivatives and Their Anion Binding Properties. Bulletin of the Korean Chemical Society 2003, 24, 661. <http://dx.doi.org/10.5012/bkcs.2003.24.5.661>
  • Yoon Dae-Wi, Hwang Hoon, Lee Chang-Hee: Synthesis of a Strapped Calix[4]pyrrole: Structure and Anion Binding Properties. Angew Chem 2002, 114, 1835. <http://dx.doi.org/10.1002/1521-3757(20020517)114:10<1835::AID-ANGE1835>3.0.CO;2-C>
  • Yoon Dae-Wi, Hwang Hoon, Lee Chang-Hee: Synthesis of a Strapped Calix[4]pyrrole: Structure and Anion Binding Properties. Angew Chem Int Ed 2002, 41, 1757. <http://dx.doi.org/10.1002/1521-3773(20020517)41:10<1757::AID-ANIE1757>3.0.CO;2-0>
  • Pichierri Fabio, Wang Liming, Zhang Jingsong, Cao Xiaoyan, Dolg Michael: Halide anion recognition by calix[4]pyrrole: a quantum chemical study. Journal of Molecular Structure: THEOCHEM 2002, 581, 117. <http://dx.doi.org/10.1016/S0166-1280(01)00749-7>
  • Chen Qingqi, Wang Tianyu, Zhang Yi, Wang Qiuan, Ma Jinshi: A FACILE, HIGHLY EFFICIENT SYNTHESIS OF FULLY N-CONFUSED CALIX[5]PYRROLE. Synth Common 2002, 32, 1041. <http://dx.doi.org/10.1081/SCC-120003152>
  • Chen Qingqi, Wang Tianyu, Zhang Yi, Wang Qiuan, Ma Jinshi: DOUBLY N-CONFUSED CALIX[4]PYRROLE PREPARED BY RATIONAL SYNTHESIS. Synth Common 2002, 32, 1051. <http://dx.doi.org/10.1081/SCC-120003153>
  • Gale Philip A.: Anion receptor chemistry: highlights from 1999. Coord Chem Rev - 2001, 213, 79. <http://dx.doi.org/10.1016/S0010-8545(00)00364-7>
  • Nagarajan Arumugam, Ka Jae-Won, Lee Chang-Hee: Synthesis of expanded calix[n]pyrroles and their furan or thiophene analogues. Tetrahedron 2001, 57, 7323. <http://dx.doi.org/10.1016/S0040-4020(01)00719-0>
  • Miyaji Hidekazu, An Deqiangan, Sessler Jonathan L.: Mono Halogen Substituted Calix[4]pyrroles: Fine-tuning the Anion Binding Properties of Calix[4]pyrrole. Supramol Chem 2001, 13, 661. <http://dx.doi.org/10.1080/10610270108027495>
  • Král Vladimír, Sessler Jonathan L., Zimmerman Rebecca S., Seidel Daniel, Lynch Vincent, Andrioletti Bruno: Calixphyrins: Novel Macrocycles at the Intersection between Porphyrins and Calixpyrroles. Angew Chem 2000, 112, 1097. <http://dx.doi.org/10.1002/(SICI)1521-3757(20000317)112:6<1097::AID-ANGE1097>3.0.CO;2-U>
  • Miyaji Hidekazu, Sato Wataru, Sessler Jonathan L.: Naked-Eye Detection of Anions in Dichloromethane: Colorimetric Anion Sensors Based on Calix[4]pyrrole. Angew Chem 2000, 112, 1847. <http://dx.doi.org/10.1002/(SICI)1521-3757(20000515)112:10<1847::AID-ANGE1847>3.0.CO;2-G>
  • Arumugam Nagarajan, Jang Yong-Sung, Lee Chang-Hee: Convenient Route to Super-Expanded Calixpyrroles:  Synthesis of Calix[n]furano[m]pyrroles (n = 3, 4, 6, 8 and m = 2, 4). Org Lett 2000, 2, 3115. <http://dx.doi.org/10.1021/ol0063196>