198 Topics in Current Chemistry Editorial Board: A. de Meijere KN ...

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126 R.E. Meléndez · A.D. Hamilton Fig. 32. The crystal structure of 48 forms a sheet through Cl◊◊◊N interactions Fig. 33. The iodo◊◊◊nitro synthon has been used in the design of tapes 49–52 49 50 51 52 based on the iodo◊◊◊nitro polarization induced interaction. The iodo◊◊◊nitro synthon has been separated by different spacers; in this case the carboxylic acid dimer has also been included. In order to design a non-centrosymmetric crystal, 4-iodo-4¢-nitrobiphenyl (52) was prepared. The molecular chirality of the twisted biphenyl units and the parallel orientation of the ribbons lead to crystal chirality.This crystalline compound is second harmonic generation active.It has also been shown that this polarized interaction prevails in the structure of 52, due to the twisted biphenyl, which gives chirality to the structure [83] (Fig. 33). 48
Hydrogen-Bonded Ribbons, Tapes and Sheets as Motifs for Crystal Engineering 127 4 Conclusion In summary, we have shown that a wide range of molecular subunit shapes and orientations can be used to generate designed packing arrangements in the solid state. A key feature of these approaches is the exploitation of well defined and directional intermolecular interactions. In several cases, certain recognition motifs have been borrowed from solution based host-guest chemistry to impart the necessary control and specificity on multicomponent aggregation in the solid state. Both strong and weak hydrogen bonding interactions have been used extensively to produce ordered tapes, ribbons, and sheets. As a result, new solid materials with functional physical and chemical properties have been produced. These have included polar crystals with non-linear optical properties, as well as porous solids with well defined cavities that can selectively complex and even catalyze reactions of small organic molecules. Acknowledgment. The portions of this work carried out at the University of Pittsburgh and Yale University were supported by the National Science Foundation (CHE 9213937). 5 References 1. Schmidt GMJ (1971) Pure Appl Chem 27:647 2. Desiraju GR (1989) Crystal engineering, the design of organic solids. Elsevier,Amsterdam 3. Lehn J-M (1988) Angew Chem Int Ed Engl 27:89 4. Dunitz JD (1991) Pure Appl Chem 63:177 5. Braga D, Grepioni F (1994) Acc Chem Res 27:51 6. Hulliger J (1994) Angew Chem Int Ed Engl 33:143 7. Vainshtein BK, Fridkin VM, Indenbom VL (1994) Structure of crystals, 2nd edn. Springer, Berlin 8. Desiraju GR (1995) The crystal as a supramolecular entity. Wiley, Chichester 9. Aakeröy CB, Seddon KR (1993) Chem Soc Rev 22:397 10. Zaworotko MJ (1994) Chem Soc Rev 283 11. Maddox J (1988) Nature 335:201 12. Wald G (1954) Sci Am 191:44 13. Lawrence DS, Jiang T, Levett M (1995) Chem Rev 95:2229 14. Fyfe MCT, Stoddart JF (1997) Acc Chem Res 30:393 15. Desiraju GR (1995) Angew Chem Int Ed Engl 34:2311 16. Leiserowitz L (1976) Acta Crystallogr B32:775 17. Leiserowitz L, Schmidt GMJ (1969) J Chem Soc 2372 18. Garcia-Tellado F, Geib SJ, Goswami S, Hamilton AD (1991) J Am Chem Soc 113:9265 19. Lady JH, Whetsel KB (1964) J Phys Chem 68:1001 20. MacDonald JC, Whitesides GM (1994) Chem Rev 94:2383 21. Panunto TW, Urbánczyk-Lipkowska Z, Johnson R, Etter MC (1987) J Am Chem Soc 109:7786 22. Herbstein FH (1996) 1,3,5-Benzenetricarboxylic acid (trimesic acid) and some analogues. Lehn J-M,Atwood JL et al. (eds) In: Solid state supramolecular chemistry: crystal engineering. Pergamon, New York, chap 3. See also: Herbstein FH (1987) In: Weber E (ed) Molecular inclusion and molecular recognition – clathrates I. Topics in Current Chemistry, vol 140. Springer, Berlin Heidelberg New York, p 107 23. Etter MC, Frankenbach GM (1989) Chem Mater 1:10
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198 Topics in Current Chemistry Edi
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Design of Organic Solids Volume Edi
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Volume Editors Prof. Dr. Edwin Webe
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VIII preface tion at an amazing lev
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Contents of Volume 196 Carbon Rich
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2 J.P. Glusker 5 Interactions of Pl
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4 J.P. Glusker Perturbations to the
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6 J.P. Glusker 2.1 Sources of Cryst
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8 J.P. Glusker other induced, will
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10 J.P. Glusker The forces here hav
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12 J.P. Glusker lographic structure
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14 J.P. Glusker a c Fig. 6 a - c. D
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16 J.P. Glusker hydrogen bond H◊
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18 J.P. Glusker Fig. 9. Citric acid
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20 J.P. Glusker peptide plane and a
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22 J.P. Glusker 4.5 F◊◊◊H Int
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24 J.P. Glusker rine-containing com
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26 J.P. Glusker Fig. 17. The packin
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28 J.P. Glusker bind to a metal ion
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30 J.P. Glusker As for carboxylate
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32 J.P. Glusker Fig. 24. The magnes
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34 J.P. Glusker structures of magne
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36 J.P. Glusker b a Fig. 28 a, b. A
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38 J.P. Glusker Fig. 30. Complexati
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40 J.P. Glusker 7.1 Descriptions of
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42 J.P. Glusker Fig. 34. Glycine cr
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44 J.P. Glusker bonding capabilitie
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46 J.P. Glusker 2. Non-intercalativ
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48 J.P. Glusker d Fig. 37 d. The ch
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50 J.P. Glusker Fig. 39. Hydrogen-b
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52 J.P. Glusker 72, 104], but other
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54 J.P. Glusker 23. Cody V, Murray-
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56 J.P. Glusker: Directional Aspect
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58 A. Nangia · G.R. Desiraju 7 Sup
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60 A. Nangia · G.R. Desiraju elect
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62 A. Nangia · G.R. Desiraju 14 15
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64 A. Nangia · G.R. Desiraju [23]
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66 A. Nangia · G.R. Desiraju struc
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68 A. Nangia · G.R. Desiraju Fig.
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70 A. Nangia · G.R. Desiraju -NH 2
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72 A. Nangia · G.R. Desiraju ingfu
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Crystalline Polymorphism of Organic
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Author Index Volumes 151-198 Author
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Author Index Volumes 151 - 198 2 ]
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Springer and the environment At Spr
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