First synthesis of an expanded calixpyrrole
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas, United StatesTetrahedron Letters (Impact Factor: 2.38). 12/1997; 38(49):8443-8444. DOI: 10.1016/S0040-4039(97)10275-1
The synthesis of the first expanded calixpyrrole: a calixarene-capped calixpyrrole 2 has been achieved using p-tert-butylcalixarene pentamethyl ketone 1 as a template. (C) 1997 Elsevier Science Ltd.
Article: Calixpyrroles II[Show abstract] [Hide abstract]
ABSTRACT: This review article is the second in a series covering advances in the synthetic and molecular recognition chemistry of calixpyrrole macrocycles (meso-octasubstituted porphyrinogens). Significant progress has been made in the last three years in the use of calixpyrroles as redox-active or optical sensors for anions. This period has also been marked by a number of preparative advances, including the synthesis of N-confused calixpyrroles, the synthesis of extended cavity calixpyrroles, and the synthesis of ‘higher order’ or ‘expanded’ calix[n]pyrroles (n>4).
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ABSTRACT: This review describes covalent and non-covalent combinations of building blocks, e.g. calixarenes, resorcinarenes, cyclodextrins, porphyrins, and cyclotriveratrylenes, leading to well-defined large (receptor) molecules.
Article: Functionalized Calixpyrroles[Show abstract] [Hide abstract]
ABSTRACT: The synthesis and properties of a number of functionalized calixpyrroles are described. To date, two generalized preparative approaches have been pursued. The first involves modifying the basic pyrrole-plus-ketone synthesis of calixpyrrole by using modified precursors or by co-condensing more than one ketone with pyrrole. The second approach relies on the reaction of a pre-formed calixpyrrole with an electrophile. In both cases, the resulting species can be subject to further manipulation. In this way a range of structures, including ones bearing ancillary recognition subunits, electro- or photochemical reporter groups, and/or water solubilizing substituents may be obtained. Solid supports bearing calixpyrroles may also be produced in this way.
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