Crystal engineering: Solid state supramolecular synthesis

Current Opinion in Solid State and Materials Science

Volumn 2, Issue 4, 1997, Pages 451-454

  Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

NLO nonlinear optical

Indexed keywords

EID: 0000382986     PISSN: 13590286     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-0286(97)80088-5     Document Type: Article

References (35)

1. Gavezzotti A. Organic crystals: engineering and design. Curr Opin Solid State Mater Sci. 1:1996;501-505 Though nominally a review, this short paper contains many original ideas that are discussed with the caution and scholarship that are a hallmark of the author.
2. Steiner T. C-HO Hydrogen bonding in crystals. Cryst Rev. 6:1996;1-57.
3. Desiraju GR. The C-HO hydrogen bond; structural implications and supramolecular design. Accounts Chem Res. 29:1996;441-449.
4. Allen FH, Howard JAK, Hoy VJ, Desiraju GR, Reddy DS, Wilson CC. First neutron diffraction analysis of an O-Hπ hydrogen bond. 2-Ethynyladamantan-2-ol. J Am Chem Soc. 118:1996;4081-4084.
5. Steiner T, Lutz B, van der Maas J, Veldman N, Schreurs AMM, Kroon J, Kanters JA. Spectroscopic evidence for cooperativity effects involving C-HO hydrogen bonds: crystalline mestranol. Chem Commun. 1997;191-192.
6. Batsanov AS, Davidson MG, Howard JAK, Lamb S, Lustig C. Phosphonium ylides as hydrogen bond acceptors: intermolecular C-HC interactions in the crystal structure of triphenylphosphonium benzylide. Chem Commun. 1996;1791-1792.
7. Howard JAK, Hoy VJ, O'Hagan D, Smith GT. How good is fluorine as a hydrogen bond acceptor? Tetrahedron. 52:1996;12613-12622.
8. Dunitz JD, Taylor R. Organic fluorine hardly ever accepts hydrogen bonds. Chem Eur J. 3:1997;89-98 In this provocative paper that raises almost as many questions as it answers, the authors use Cambridge database analysis and ab initio perturbation theory and contend that it is difficult for covalently bound fluorine to act as a hydrogen bond acceptor. These matters are particularly contentious as even the value of the van der Waals radius for fluorine is subject to dispute.
9. Schwiebert KE, Chin DN, MacDonald JC, Whitesides GM. Engineering the solid state with 2-benzimidazolones. J Am Chem Soc. 118:1996;4018-4029.
10. Lewis FD, Yang J-S, Stern CL. Crystal structures of secondary arenecarboxamides: an investigation of arene - hydrogen bonding relationships in the solid state. J Am Chem Soc. 118:1996;12029-12037.
11. Coe S, Kane JJ, Nguyen TL, Toledo LM, Wininger E, Fowler FW, Lauher JW. Molecular symmetry and the design of molecular solids: the oxalamide functionality as a persistent hydrogen bonding unit. J Am Chem Soc. 119:1997;86-93.
12. Reddy DS, Ovchinnikov YE, Shishkin OV, Struchkov YT, Desiraju GR. Supramolecular synthons in crystal engineering. 3. Solid state architecture and synthon robustness in some 2,3-dicyano-5,6-dichloro-1,4-dialkoxybenzenes. J Am Chem Soc. 118:1996;4085-4089.
13. Zafar A, Yang J, Geib SJ, Hamilton AD. Linked bis-isophthalic acid derivatives as building blocks in the design of self-assembling structures. Tetrahedron Lett. 37:1996;2327-2330.
14. 3-1,3,5·1'5(4,4′-bipy): a 'super trimesic acid' chicken-wire grid. Chem Commun. 1996;2655-2656.
15. Yaghi OM, Li H, Groy TL. Construction of porous solids from hydrogen-bonded metal complexes of 1,3,5-benzenetricarboxylic acid. J Am Chem Soc. 118:1996;9096-9101.
16. Glidewell C, Ferguson G. Interpenetrating square nets in the hydrogen-bonded structure of 4,4′-sulfonyldiphenol. Acta Crystallogr C. 52:1996;2528-2530.
17. Bock H, Seitz W, Sievert M, Kleine M, Bats JW. Donor/acceptor complexes in hydrogen-bonded networks: pH-dependent self-organization. Angew Chem Int Ed. 35:1996;2244-2246.
18. Black DStC, Craig DC, McConnell DB. The indol-2-ylglyoxylamide moiety: a new building block for the design and self-assembly of hydrogen bonded networks. J Am Chem Soc. 118:1996;8148-8149.
19. Mascal M, Hext NM, Warmuth R, Moore MH, Turkenburg JP. Programming a hydrogen-bonding code for the specific generation of a supermacrocycle. Angew Chem Int Ed. 35:1996;2204-2206.
20. Hoss R, König O, Kramer-Hoss V, Berger U, Rogin P, Hulliger J. Crystallization of supramolecular materials: perhydrotriphenylene (PHTP) inclusion compounds with nonlinear optical properties. Angew Chem Int Ed. 35:1996;1664-1666.
21. Pan F, Wong MS, Gramlich V, Bosshard C, Günter P. Crystal engineering based on short hydrogen bonds; cocrystallisation of a highly nonlinear optical merocyanine dye with nitrophenol derivatives. Chem Commun. 1996;1557-1558.
22. Pan F, Wong MS, Gramlich V, Bosshard C, Günter P. A novel and perfectly aligned highly electro-optic organic cocrystal of a merocyanine dye and 2,4-dihydroxybenzaldehyde. J Am Chem Soc. 118:1996;6315-6316.
23. Nicoud J-F, Masse R, Bourgogne C, Evans C. Perfect layered arrangement of ion-paired chromophores in a crystalline non-linear optical organic salt: 2-amino-3-nitropyridinium chloride. J Mater Chem. 7:1996;35-39.
24. Sarma JARP, Allen FH, Hoy VJ, Howard JAK, Thaimattam R, Biradha K, Desiraju GR. Design of an SHG-active crystal, 4-iodo-4′-nitrobiphenyl: the role of supramolecular synthons. Chem Commun. 1997;101-102.
25. Voigt-Martin IG, Li G, Yakimanski A, Schulz G, Wolff JJ. The origin of nonlinear optical activity of 1,3,5-triamino-2,4,6-trinitrobenzene in the solid state: the crystal structure of a non-centrosymmetric polymorph as determined by electron diffraction. J Am Chem Soc. 118:1996;12830-12831.
26. Kräutler B, Müller T, Maynollo J, Gruber K, Kratky C, Ochsenbein P, Schwarzenbach D, Bürgi H-B. A topochemically controlled, regiospecific fullerene bisfunctionalisation. Angew Chem Int Ed. 35:1996;1204-1206.
27. Brunet P, Simard M, Wuest JD. Molecular tectonics. Porous hydrogen-bonded networks with unprecedented structural integrity. J Am Chem Soc. 119:1997;2737-2738 Molecules whose interactions are dominated by specific attractive forces are called 'tectons' by Wuest. Accordingly 'molecular tectonics' is the art and science of supramolecular construction using tectonic subunits. Note that while terms such as motif, pattern and synthon are inherently supramolecular in character, 'tecton' is unashamedly molecular. However, this creates problems because, in the limit, all crystals are built with specific attractive forces leading to the trivial conclusion that all molecules are tectons. The characterization of a molecule as a tecton is therefore somewhat subjective.
28. Allen FH, Hoy VJ, Howard JAK, Thalladi VR, Desiraju GR, Wilson CC, McIntyre GJ. Crystal engineering and correspondence between molecular and crystal structures. Are 2- and 3-aminophenols anomalous? J Am Chem Soc. 119:1997;3477-3480.
29. Reddy DS, Craig DC, Desiraju GR. Supramolecular synthons in crystal engineering. 4. Structure simplification and synthon interchangeability in some organic diamondoid solids. J Am Chem Soc. 118:1996;4090-4093.
30. Gavezzotti A, Filippini G. Computer prediction of organic crystal structures using partial X-ray diffraction data. J Am Chem Soc. 118:1996;7153-7157.
31. Chaka AM, Zaniewski R, Youngs W, Tessier C, Klopman G. Predicting the crystal structure of organic molecular materials. Acta Crystallogr B. 52:1996;165-183.
32. Pedireddi VR, Jones W, Chorlton AP, Docherty R. Creation of crystalline supramolecular arrays: a comparison of co-crystal formation from solution and by solid-state grinding. Chem Commun. 1996;987-988.
33. Perlstein J, Steppe K, Vaday S, Ndip EMN. Molecular self-assemblies. 5. Analysis of the vector properties of hydrogen bonding in crystal engineering. J Am Chem Soc. 118:1996;8433-8443.
34. Aoyama Y, Endo K, Anzai T, Yamaguchi Y, Sawaki T, Kobayashi K, Kanehisa N, Hashimoto H, Kai Y, Masuda H. Crystal engineering of stacked aromatic columns. Three-dimensional control of the alignment of orthogonal aromatic triads and guest quinones via self-assembly of hydrogen-bonded networks. J Am Chem Soc. 118:1996;5562-5571 One- and two-dimensional control are routinely realizable in many structural families with strong and not-so-strong intermolecular interactions. However, there are many problems at the strategic and methodological levels in going from the second to the third dimension. This paper is one of the first examples where the elements of three-dimensional control, in this case hydrogen bonding and ring stacking, have been incorporated into the design strategy in a fully deliberate manner.
35. Philp D, Stoddart JF. Self-assembly in natural and unnatural systems. Angew Chem Int Ed. 35:1996;1154-1196.