Inclusion compounds

Current Opinion in Solid State and Materials Science

Volumn 1, Issue 4, 1996, Pages 514-521

  Hollingsworth, Mark D ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002624787     PISSN: 13590286     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-0286(96)80067-2     Document Type: Article

References (44)

1. MacNicol DD: Structure and design of inclusion compounds: The hexa-hosts and symmetry considerations. In Inclusion Compounds, vol 2. Edited by Atwood JL, Davies JED, MacNicol, DD. New York: Academic Press; 1984:123-168.
2. Henderson K, MacNicol DD, Mallinson PR, Vallance 1: 2,4,6-tris[4-(1-naphthyl)phenoxy]-1,3,5-triazine: Formation of a unique piedfort-based host lattice with trigonal symmetry. Supramol Chem 1995, 5:301-304.
3. Wang X, Simard M, Wuest JD: Molecular tectonics. Three-dimensional organic networks with zeolitic properties. J Am Chem Soc 1994, 116:12119-12120. This article describes new diamondoid networks based on tetrahedral compounds bearing 2-pyridones as the hydrogen bond donors and acceptors. Some of these inclusion compounds exhibit guest exchange without concomitant changes in the lattice parameters of the host.
4. Venkataraman D, Lee S, Zhang J, Moore JS: An organic solid with wide channels based on hydrogen bonding between macrocycles. Nature 1994, 371:591-593. External phenolic ethers link hexagonal-shaped macrocycles into two-dimensional arrays. The three-dimensional packing generates channels that are filled with solvent molecules.
5. Venkataraman D, Gardner GB, Lee S, Moore JS: Zeolite-like behavior of a coordination network. J Am Chem Soc 1995, 117:11600-11601. The robust inclusion compound described here loses one-fourth of the solvent molecules from its tunnels without significant changes in unit cell constants or loss of optical clarity.
6. Toda F, Tanaka K, Imai T, Bourne SA: Design of new host compounds, cis-1,4-diphenylcyclohexane-1,4-diol, exo, exo-2,5-diphenylnorbornane-2,5-diol, exo-exo-2,6-diphenylbicyclo[3.3.1]nonane-2,6-diol and their derivatives. Supramol Chem 1995, 5:289-295.
7. Csöregh I, Gallardo O, Weber E, Dörpinghaus N: Supramolecular complexation of DMF and acetone involving singly bridged triarylmethanol and analogous hosts. X-ray crystal structures of four inclusion compounds. Supramol Chem 1995, 5:159-165.
8. Aoyama Y, Endo K, Kobayashi K, Masuda H: Hydrogen-bonded network and enforced supramoleculer cavities in molecular crystals: An orthogonal aromatic-triad strategy. Guest binding, molecular recognition, and molecular alignment properties of a bisresorcinol derivative of anthracene in the crystalline state. Supramol Chem 1995, 4:229-241.
9. Endo K, Sawaki T, Koyanagi M, Kobayashi K, Masuda H, Aoyama Y: Guest-binding properties of organic crystals having an extensive hydrogen-bonded network: An orthogonal anthracene-bis(resorcinol) derivative as a functional organic analog of zeolites. J Am Chem Soc 1995, 117:8341-8352. Numerous exchange studies are described for this versatile new inclusion system.
10. Zhang, H, Steed JW, Atwood JL: Inclusion chemistry of cyclotetraveratrylene. Supramol Chem 1995, 4:185-190.
11. Kolotuchin, SV, Fenlon EE, Wilson SR, Loweth CJ, Zimmerman SC: Self-assembly of 1,3,5-benzenetricarboxylic acids (trimesic acids) and several analogues in the solid state. Angew Chem Int Ed Engl 1995, 34:2654-2657. This article includes a discussion of catameric hydrogen bonding motifs of carboxylic acids, and is a good example of one way to reduce the interpenetration of networks in porous organic solids.
12. Ermer O, Lindenberg L: 81. Double-diamond inclusion compounds of 2,6-dimethylideneadamantane-1,3,5,7-tetracarboxylic acid. Helv Chim Acta 1991, 74:825-877.
13. Ermer O, Eling A: Molecular recognition among alcohols and amines: Super-tetrahedral crystal architectures of linear diphenol-diamine complexes and aminophenols. J Chem Soc Perkin Trans 2 1994:925-944. This is an excellent summary of Ermer's work on diamondoid and related networks.
14. Bernstein J, Davis RE, Shimoni L, Chang N-L: Patterns in hydrogen bonding: Functionality and graph set analysis in crystals. Angew Chem Int Ed Engl 1995, 34:1555-1573. An excellent overview of the relationships of graph sets to crystal engineering. This work describes important modifications in the rules for formulating graph sets, which were originally outlined by Etter [15].
15. Etter MC: Encoding and decoding hydrogen-bond patterns of organic compounds. Account Chem Res 1990, 23:120-126.
16. Gardner GB, Venkataraman D, Moore JS, Lee S: Spontaneous assembly of a hinged coordination network. Nature 1995, 374:792-795. Although the materials properties of this system were not reported, this network has the correct topology to be an auxetic solid with a negative Poisson's ratio. The solvent exchange properties of this host are notable.
17. Caira MR, Horne A, Nassimbeni LR, Okuda K, Toda F: Selective inclusion of phenylenediamine isomers by 1,1-bis(4-hydroxyphenyl)cyclohexane. J Chem Soc Perkin Trans 2 1995:1063-1067.
18. Hayashi N, Mazaki Y, Kobayashi K: Channel-to-channel rearrangements of host lattices in clathrate crystals induced by guest exchange via gas-solid contacts. Advan Mater 1994, 6:654-656.
19. Hajek F, Graf E, Hosseini MW, Delaigue X, De Cian A, Fischer J: Molecular tectonics I: The first synthesis and X-ray analysis of a linear koilate obtained by self-assembly of linear koilands and hexadiyne. Tetrahedron Lett 1996, 37:1401-1404. This paper describes the supramolecular assembly of an unusual one-dimensional molecular array in which a linear molecular connector (hexadiyne) is used to join two koilands (a hollow molecule possessing two divergent cavities).
20. Goldberg I, Krupitsky H, Stein Z, Hsiou Y, Strouse CE: Supramolecular architectures of functionalized tetraphenylmetalloporphyrins in crystalline solids. Studies of the 4-methoxyphenyl, 4-hydroxyphenyl and 4-chlorophenyl derivatives. Supramol Chem 1995, 4:203-221. An exhaustive survey of the crystallographic features of a number of porphyrin clathrates.
21. Ibragimov BT, Talipov SA, Zorky PM: Inclusion complexes of the natural product gossypol. Supramol Chem 1994, 3:147-165.
22. Welberry TR, Butler BD: Diffuse X-ray scattering from disordered crystals. Chem Rev 1995, 95:2369-2403. An excellent review on the nature of diffuse scattering of X-rays, which is a common occurence in many inclusion compound studies.
23. Brouwer EB, Enright GD, Ratcliffe CI, Ripmeester JA: Dynamic molecular recognition in solids: A synoptic approach to structure determination in p-tert-butylcalix[4]arene-toluene. Supramol Chem 1996, 7:79-83. A nice demonstration of how solid state NMR and X-ray diffraction can be combined to solve problems of static and dynamic disorder, which appear to be widespread in calix[4]arenes.
24. Brouwer EB, Enright GD, Ripmeester JA: Guest-induced asymmetry in the structure of p-tert-butylcalix[4]arene-nitrobenzene. Supramol Chem 1996, 7:7-9.
25. Van Smaalen S, Harris KDM: Superspace group descriptions of the symmetries of incommensurate urea inclusion compounds. Proc Roy Soc London Ser A 1996, 452:677-700. This article describes the application of the superspace formalism to describe the symmetries of incommensurate urea inclusion compounds.
26. Shannon IJ, Harris KDM, Guillaume F, Bocanegra EH, MacLean EJ: Phase transitions involving re-ordering of the guest molecules in a solid organic inclusion compound: Heptanoic anhydride-urea. J Chem Soc Chem Commun 1995:2341-2342.
27. Fukuo K: X-ray scattering and disordered structure of n-tetracosane in urea adducts I. A model for the X-ray scattering pattern. J Chem Phys 1994, 101:7882-7892.
28. Fukao K: X-ray scattering and disordered structure of n-tetracosane in urea adducts. II. Averaged disorder, spatial correlation, and phase transition. J Chem Phys 1994, 101:7893-7903.
29. Schmicker D, Van Smaalen S, Haas C, Harris KDM: Elastic constants of the dioctanoyl peroxide/urea inclusion compound determined by Brillouin scattering. Phys Rev B - Condens Matter 1994, 49:11572-11579.
30. Schmicker D, Van Smaalen S, De Boer JL, Haas C, Harris KDM: Observation of the sliding mode in incommensurate intergrowth compounds. Brillouin scattering from the inclusion compound of urea and heptadecane. Phys Rev Lett 1995, 74:734-737.
31. Garneau I, Raymond S, Brisse F: A thiourea-1,5-cyclooctadiene clathrate at 173K. Acta Crystallogr C - Cryst Str 1995, 51:538-541.
32. Shannon IJ, Jones MJ, Harris KDM, Siddiqui MRH, Joyner RW: Probing the conformational properties of guest molecules in solid inclusion compounds via EXAFS spectroscopy: Bromine K-edge EXAFS studies of the bromocyclohexane/thiourea and trans-1-bromo-2-chlorocyclohexane/thiourea inclusion compounds. J Chem Soc Faraday Trans 1995, 91:1497-1501.
33. Hollingsworth MD, Santarsiero BD, Harris KDM: Zigzag channels in the structure of sebaconitrile/urea. Angew Chem Int Ed Engl 1994, 33:649-652.
34. Brown ME, Hollingsworth MD: Stress-induced domain reorientation in urea inclusion compounds. Nature 1995, 376:323-327. This article shows how uniaxial stress can be used to reorient macroscopic domains of a distorted urea inclusion compound. In addition to providing a detailed mechanism of the single crystal to single crystal domain reorientation, this work shows how introduction of a tailor-made guest impurity can transform the response from a plastic one to an elastic one.
35. Hollingsworth MD, Brown ME, Santarsiero BD, Huffman JC, Goss CR: Template-directed synthesis of 1:1 layered complexes of α,ω-dinitriles and urea: Packing efficiency versus specific functional group interactions. Chem Mater 1994, 6:1227-1244. This article compares packing efficiency in crystals with and without inter-molecular hydrogen bonds, and shows how homologous series can be advantageously used in studies of crystal packing of inclusion compounds and stoichiometric complexes.
36. Hollingsworth MD, Harris KDM: Urea, thiourea and selenourea. In Comprehensive Supramolecular Chemistry. Solid State Supramolecular Chemistry: Crystal Engineering, vol 6. Edited by MacNicol DD, Toda F, Bishop R. Oxford: Elsevier Science Ltd; 1996, in press.
37. Atwood JL, Davies JED, MacNicol DD, Vogtle F (Eds). Comprehensive Supramolecular Chemistry. Oxford: Elsevier Science Ltd; 1996, in press. This important publication is due to be published in the summer of 1996. In eleven volumes, it will be a major reference work for the field for decades.
38. Hulliger J, König O, Hoss R: Polar inclusion compounds of perhydrotriphenylene (PHTP) and efficient nonlinear optical molecules. Advan Mater 1995, 7:719-721. A wide variety of NLO chromophores are incorporated as polar arrays into the channels of perhydrotriphenylene.
39. 60) is achieved by selective recrystallization in the presence of p-fert-butylcalix[8]arene.
40. Toda F: Solid state organic chemistry: efficient reactions, remarkable yields, and stereoselectivity. Account Chem Res 1995, 28:480-486. A descriptive account of reactions, molecular recognition and stereoselectivity in organic crystals and inclusion compounds.
41. 4] compounds "vapochromic" environmental sensors. Chem Mater 1995, 7:15-17.
42. Rifani M, Yin Y-Y, Elliott DS, Jay MJ, Jang S-H, Kelley, MP, Bastin, L, Kahr B: Solid state dye lasers from stereospecific host-guest interactions. J Am Chem Soc 1995, 117:7572-7573. The oriented inclusion of sulfonated pyrene and rhodamine dyes into specific growth sectors of potassium sulfate provides a new medium for the generation of blue, green, and red solid state dye lasers. Although not strictly an organic system, this system represents an exciting development in the use of organic inclusions as practical optical devices.
43. Hulliger J: Chemistry and crystal growth. Angew Chem Int Ed Engl 1994,33:143-162. An important paper describing methods of crystal growth that should be of interest to inclusion chemists.
44. Desiraju GR: Supramolecular synthons in crystal engineering - a new organic synthesis. Angew Chem Int Ed Engl 1995, 34:2311-2327. An excellent review on crystal engineering and supramolecular chemistry.