Past, Present, and Future of di Milano From Small Molecules to Macromolecules and Supramolecular Structures

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1 Past, Present, and Future of di Milano From Small Molecules to Macromolecules and Supramolecular Structures Book of Abstracts 6-7 June, 2013

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3 ... Milan Politecnico... has seen a lot of crystallography. So there is a very nice past; the present certainly is very well known in my own subject... and the future, you know, who knows what the future will bring? As I said, crystallographers and people who use crystallography need to have a very, very open mind about what the subject means. Gautam R. Desiraju President of the International Union of Crystallography 6 June 2013, Opening remarks to the Conference 6-7 June 2013, Milan, Italy I

4 6-7 June 2013, Milan, Italy II

5 In 2013 the Politecnico di Milano celebrated its 150 th anniversary ( ) also marked the 50 th anniversary of the award of the Nobel Prize in chemistry to Giulio Natta, for his discoveries at the Politecnico di Milano in the field of the chemistry and technology of high polymers. In this framework, the conference Past, Present and Future of di Milano: From Small Molecules to Macromolecules and Supramolecular Structures was held on 6-7 June, 2013 at Politecnico di Milano. The event celebrated the two above mentioned important milestones for Chemistry and for our university. The conference brought together leading scientists with interests in crystallography and crystal engineering, providing an excellent opportunity to disseminate the latest results in the field. ORGANIZING COMMITTEE Pierangelo Metrangolo, Politecnico di Milano Giuseppe Resnati, Politecnico di Milano Gabriella Cavallo, Politecnico di Milano Giancarlo Terraneo, Politecnico di Milano SCIENTIFIC SECRETARIAT Johanna Syvanen, Politecnico di Milano 6-7 June 2013, Milan, Italy III

6 6-7 June 2013, Milan, Italy IV

7 Past, Present and Future of di Milano: From Small Molecules to Macromolecules and Supramolecular Structures Organized under the auspices of: IUCr (IYCr 2014) AIC AICIng In collaboration with: FluorIT Sponsored by: IUPAC 6-7 June 2013, Milan, Italy V

8 ACS RSC CrystEngComm Bruker Sigma Aldrich Fondazione Cariplo Politecnico di Milano DCMIC 6-7 June 2013, Milan, Italy VI

9 SCIENTIFIC PROGRAM ORAL PRESENTATION - THURSDAY, JUNE 6, 2013 SESSION I Chairman: Kari Rissanen LIQUID ENGINEERING TO CRYSTAL ENGINEERING: HOW IONIC LIQUIDS CAN HELP US MASTER THE PHARMACEUTICAL SOLID STATE R. D. Rogers, S. P. Kelley LIQUID-CRYSTAL ENGINEERING: FROM MOLECULES TO MATERIALS A. Crispini, D. Pucci, N. Godbert, M. La Deda, I. Aiello, M. Ghedini CRYSTAL ENGINEERING OF PHARMACEUTICAL CO-CRYSTALS V. Ferretti p. 11 p. 12 p. 13 SESSION II Chairman: Giuseppe Resnati SMART(LY DESIGNED) MATERIALS M. J. Zaworotko INTERMOLECULAR INTERACTIONS IN MOLECULE-BASED MAGNETS: LONG-DISTANCE BONDS BETWEEN RADICAL-IONS M. Fumanal, M. Capdevila, J. S. Miller, J. J. Novoa ORGANIC MACROCYCLES FOR DESIGNING POROUS MATERIALS C. Tedesco p. 16 p. 17 p. 18 SESSION III Chairman: Mir Wais Hosseini CRYSTALLOGRAPHY OF LARGE SUPRAMOLECULAR COMPLEXES K. Rissanen CRYSTALLOGRAPHY AND SUPRAMOLECULAR SENSING C. Massera, E. Biavardi, R. Pinalli, F. Ugozzoli, E. Dalcanale NETWORK ANALYSIS IN CRYSTAL ENGINEERING, MORE THAN A DULL TAXONOMY EXERCISE L. Öhrström p. 20 p. 21 p June 2013, Milan, Italy 1

10 MOLECULAR RECOGNITION OF SMALL GUESTS BY CRYSTALLINE SUPRAMOLECULAR SYSTEMS: FROM LOCAL CONTROL TO COLLECTIVE BEHAVIOUR AND BACK A. Bacchi, P. Pelagatti p. 23 SESSION IV Chairman: Robin D. Rogers CRYSTALLOGRAPHY AND BIOMINERALIZATION: ON CRYSTALS, DISORDERED PHASES, AND THEIR TRANSFORMATIONS L. Addadi, A. Akiva, D. Gur, A. Gal, S. Weiner STRUCTURE-BASED SOLID-STATE FORM DESIGN: IDENTIFYING COMMERCIALLY-VIABLE CRYSTAL FORMS FOR HIGH QUALITY DRUG PRODUCTS S. M. Reutzel-Edens MULTIPLE CRYSTAL FORMS: SWORD OF DAMOCLES OR AN OPPORTUNITY FOR THE PHARMA INDUSTRY? F. Grepioni POROSITY IN FLEXIBLE METAL-ORGANIC SYSTEMS L. Barbour p. 26 p. 27 p. 28 p. 29 ORAL PRESENTATION - FRIDAY, JUNE 7, 2013 SESSION V Chairman: Mike Zaworotko SELF-ASSEMBLIES FOR BIOMIMETIC MATERIALS O. Ikkala POROUS COORDINATION NETWORKS: STRUCTURES, ENTANGLEMENTS AND PROPERTIES L. Carlucci, G. Ciani, D. M. Proserpio RECOGNITION AND SENSING WITH POLYAMINE-BASED HOSTS: STRUCTURAL ASPECTS P. Paoli p. 32 p. 33 p June 2013, Milan, Italy 2

11 SESSION VI Chairman: Pierangelo Metrangolo FROM TECTONS TO CRYSTALS OF CRYSTALS M. W. Hosseini AT THE LIMITS OF IN SITU CRYSTALLIZATION FOR STRUCTURE DETERMINATION R. Boese IN SITU CRYOCRYSTALLIZATION OF HALOGEN BONDED SUPRAMOLECULAR COMPLEXES G. Terraneo, G. Cavallo, T. Pilati, P. Metrangolo, G. Resnati FLUORINE AND DEUTERIUM: INFLUENCE ON THE CRYSTAL ARCHITECTURE. V. Vasylyeva, K. Merz, O. V. Shishkin p. 36 p. 37 p. 39 p June 2013, Milan, Italy 3

12 6-7 June 2013, Milan, Italy 4

13 POSTERS P1 P2 P3 P4 SUPRAMOLECULAR INTERACTIONS AS GLUE FOR THE DESIGN OF SMART ARCHITECTURES I. Bassanetti, A. Comotti, S. Bracco, L. Marchio, P. Sozzani POROUS DIPEPTIDE CRYSTALS AND ORGANIC FRAMEWORKS AS POLYMERIZATION VESSELS M. Beretta, A. Comotti, S. Bracco, P. Sozzani NEW HYBRID ORGANIC-ORGANOMETALLIC NANO-RIBBONS R. Bertani, P. Sgarbossa, V. Di Noto, M. Piga, G. Giffin, G. Terraneo, T. Pilati, P. Metrangolo, G. Resnati SYNTHESIS OF A COUMARIN - NBD CALIX[4]ARENE SYSTEM AND SPECTROSCOPIC STUDY OF ITS ENERGY TRANSFER PROPERTIES I. Tosi, L. Baldini, S. Bertella, F. Sansone, F. Terenziani p. 42 p. 43 p. 44 p. 45 P5 X-RAY DIFFRACTION IS THE EXPERIMENTAL ARM OF CRYSTALLOGRAPHY. KNOWN AND UNKNOWN TRIBUTE OF PISA FROM LAST TOWARDS NEXT TWENTIES G. Berti, F. De Marco, S. Aldrighetti P6 THE EFFECT OF THE FLUORINE SUBSTITUTION ON SUPRAMOLECULAR ASSEMBLIES OF ARYL BENZYL SULFOXIDES C. Cardellicchio, M. A. M. Capozzi, F. Capitelli p. 46 p. 47 P7 ACTIVATION OF ROOM TEMPERATURE PHOSPHORESCENCE OF ORGANIC CO-CRYSTALS. A NOVEL APPROACH BASED ON HALOGEN-BOND. L. Catalano, A. Bertocco, S. D'Agostino, B. Ventura, F. Grepioni, D. Braga p. 48 P8 FLUORINATED METAL-ORGANIC FRAMEWORKS SELF- ASSEMBLED VIA HALOGEN BOND L. Colombo, P. Metrangolo, T. Pilati, G. Resnati, G. Terraneo P9 CRYSTAL STRUCTURE AND OPTICAL PROPERTIES OF FLUORINATED PUSH-PULL J-AGGREGATES V. Dichiarante, E. Cariati, G. Cavallo, A. Forni, P. Metrangolo, T. Pilati, G. Resnati, G. Terraneo P10 DESMOTROPY, POLYMORPHISM AND SOLID-STATE PROTON TRANSFER: FOUR SOLID FORMS OF AN AROMATIC O-HYDROXY SCHIFF BASE I. ilovi, M. Rub i, K. Užarevi, I. Halasz, N. Bregovi, M. Mališ, Z. Kokan, R. S. Stein, R. E. Dinnebier, V. Tomiši p. 49 p. 50 p June 2013, Milan, Italy 5

14 P11 P12 DESIGN, SYNTHESIS AND CHARACTERIZATION OF LUMINESCENT COPPER(I)-IODIDE COMPLEXES FOR OPTOELECTRONIC DEVICES F. Farinella, P. P. Mazzeo, L. Maini, D. Braga ORGANIC FRAMEWORKS FORMED VIA HYDROGEN AND HALOGEN BONDING ORTHOGONAL SELF-ASSEMBLY F. Fernandez-Palacio, L. Colombo, J. Martí-Rujas, G. Terraneo, T. Pilati, P. Metrangolo, G. Resnati p. 52 p. 53 P13 LCDIXRAY: POWDER DIFFRACTION INDEXING OF COLUMNAR LIQUID CRYSTALS N. Godbert, A. Crispini, M. Ghedini, M. Carini, F. Chiaravalotti, A. Ferrise p. 54 P14 P15 P16 P17 P18 P19 REAL-TIME IN SITU X-RAY DIFFRACTION MONITORING OF MECHANOCHEMICAL FORMATION OF MODEL ORGANIC PHARMACEUTICAL COCRYSTAL I. Halasz, A. Puškari, S. A. J. Kimber, P. J. Beldon, F. Adams, V. Honkimäki, R. E. Dinnebier, V. Štrukil, T. Friš i STRUCTURAL STUDIES OF SUPRAMOLECULAR GYROSCOPE-LIKE CO-CRYSTALS J. Lin, C. M. Widdifield, G. Cavallo, G. A. Facey, T. Pilati, P. Metrangolo, G. Resnati, D. L. Bryce ON THE ROLE OF HYDROGEN BOND IN THE CRYSTAL PACKING OF RU (II) HALF-SANDWICH COMPLEXES C. Loffi, P. Pelagatti, A. Bacchi, P. Swuec A VOYAGE IN THE B VITAMINS WORLD: B 6 AS NOVEL LIGAND IN CLUSTER CHEMISTRY AND NEW DISCOVERIES IN THE FIELD OF B 12 CRYSTALLOGRAPHY. N. Marino, D. Armentano, G. De Munno, R. P. Doyle SUPRAMOLECULAR GELS FORMATION INDUCED BY HALOGEN BONDING L. Meazza, J. A. Foster, K. Fucke, P. Metrangolo, G. Resnati, J. W. Steed. POLYMORPHISM AND SOLID FORMS IN 1,1,4,4-TETRAPHENYL-1,3- BUTADIENE. A. Monica, A. Bacchi, M. Masino, D. Crocco p. 55 p. 56 p. 57 p. 58 p. 59 p. 60 P20 PICTURING THE INDUCED FIT OF CALIX[5]ARENES UPON N-ALKYLAMMONIUM CATION BINDING A. Notti, G. Gattuso, S. Pappalardo, M. F. Parisi, T. Pilati, G. Resnati, G. Terraneo p June 2013, Milan, Italy 6

15 P21 TRAVELLING WITH POLYMORPHS: THE CASE OF TETRAPENTOXYCALIX[4]ARENE A. G. Ricciardulli, M. Lusi, L. Erra, C. Gaeta, C. Talotta, P. Neri, L. J. Barbour, C. Tedesco p. 62 P22 P23 FUNCTIONAL GROUP EFFECT ON THE CLATHRATING PROPERTIES OF HALF-SANDWICH RU (II) COMPLEX F. Scè, A. Bacchi, P. Pelagatti PT(II)-IMINO DERIVATIVES: DIMERS AND OLIGOMERS AS A SUPPLY OF CYTOTOXIC AGENTS P. Sgarbossa, R.A. Michelin, R. Bertani, M. Mozzon, C. Marzano, V. Gandin p. 63 p. 64 P24 ZNO NANOPARTICLES SYNTHESIS WITH CONTROLLED MORPHOLOGY (SHAPE & SIZE) BY USING NATURAL BIODEGRADABLE POLYMER S. U. Shisodia, A. Citterio, V. V. Chabukswar, N. S. Pande, V. Purohit, S. V. Bhavsar, K. N. Hondore, K. C. Mohite p. 65 P25 P26 CRYSTALLIZATION OF TWO ISOMERIC AMINOACIDS FROM SOLUTION AND FROM GEL F. Silvestri, D. Crocco, A. Bacchi A NANOPOROUS CRYSTALLINE STRUCTURE GENERATED BY A TIOUREA-BASED CALIX[6]ARENE F. Ugozzoli, A. Arduini, R. Bussolati, C. Massera, F. Rapaccioli, A. Secchi p. 66 p. 67 P27 SELECTIVE MECHANOCHEMISTRY: FLEXIBLE MOLECULAR RECEPTORS FOR RECOGNITION OF ORGANIC ISOMERS IN MILLING PROCESSES K. Užarevi, I. Halasz, I. ilovi, M. Rub i, N. Bregovi p. 68 POSTER PRIZE WINNERS p. 70 AUTHOR INDEX p June 2013, Milan, Italy 7

16 6-7 June 2013, Milan, Italy 8

17 ORAL PRESENTATIONS 6-7 June 2013, Milan, Italy 9

18 SESSION I Chairman: Kari Rissanen 6-7 June 2013, Milan, Italy 10

19 Liquid Engineering to Crystal Engineering: How Ionic Liquids Can Help Us Master the Pharmaceutical Solid State R. D. Rogers, S. P. Kelley Center for Green Manufacturing and Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487, USA address: The pharmaceutical industry relies mainly on the solid forms of active pharmaceutical ingredients (APIs) for drug delivery, which has resulting in increasing instances of problems such as polymorphic conversion, low solubility, and low bioavailability which are associated with solid compounds. This has led to a major effort to create marketable new drugs by improving the properties of already known APIs by designing new solid forms through strategies such as salt formation, co-crystallization, and polymorph screening, but these approaches have brought new challenges such as the regulatory classification of multicomponent solids which are neither completely ionic nor completely neutral. However, the strategy of avoiding the solid state entirely through the use of low melting salts (ionic liquids, or ILs) has received less attention. ILs are highly tunable liquids which have been applied to drug delivery through strategies ranging from solvating and dispersing agents for poorly soluble drugs to bypassing the solid state altogether by making API salts into compounds that form neat liquids at low temperatures. It is time for the pharma sector to learn more about the potential impact of ILs in virtually every phase of drug discovery, manufacture, and delivery. A more fundamental, systems view of ILs is needed to overcome hesitation in using them by obtaining an appreciation of the true power of IL design to purpose. ILs have utility in the manufacture of APIs, delivery of APIs, and even as APIs. IL APIs even have a role in expanding the understanding of crystal engineering as they offer a dynamic liquid environment in which to study the effects of ionicity on the physicochemical properties of a neat API compound as a complement to the solid state. In this presentation, several aspects of the IL form of matter will be discussed to illustrate the broad utility of these materials in the pharma industries which can be realized by adopting an Ionic Liquid way of thinking. Figure 1: Roles of ILs throughout the API design and delivery process 6-7 June 2013, Milan, Italy 11

20 Liquid-Crystal Engineering: From Molecules to Materials A. Crispini 1, D. Pucci 1, N. Godbert 1, M. La Deda 1, I. Aiello 1, M. Ghedini 1 1 Department of Chemistry and Chemica Technologies, University of Calabria, Italy. The self-assembly of suitable building-blocks, through inter- or intra-molecular interactions of different nature, is a current approach to get new nanostructure materials, amongst which liquid crystals are particularly intriguing due to their ordered yet dynamic structures [1]. The synthesis of liquid crystals based on metal complexes (metallomesogens) has received great attention since the metal centre is able to promote mesomorphism in non mesogenic ligands. Significant progress has been made in the field of metallomesogens, by modulating factors such as nano-segregation, molecular motifs functional to specific intermolecular interactions and molecular shapes [2]. In this context, we have devoted our studies towards the careful choice of various molecular frameworks in the modulation of interactions responsible for the supramolecular architectures suitable in metalcontaining liquid crystalline molecular materials [3]. This communication will illustrate examples chosen from our library of metallomesogens, proving our liquid-crystal engineering approach in the modulation of molecular shape (by changing the metal ions and the organic ligands) and non covalent interactions (by changing substituents on the molecular organic fragments). A deep study of their molecular organization both in the crystalline solid state and the liquid crystalline phases, conducted through single crystal and variable temperature powder X ray analyses, will be presented in order to highlight the relationships between structure and mesomorphic behaviour based on non covalent interactions. Figure 1: PXRD pattern of an unconventional Pd-mesogen in its hexagonal phase and derived crystal packing [3] References 1. T. Kato, Chem. Commun., 2009, Metallomesogens In Comprehensive Coordination Chemistry II: From Biology to Nanotechnology, Vol. 7 (Eds.: J. A. McCleverty, T. J. Meyer, M. Fujita, A. Powell) Elsevier, Oxford, 2003, ch. 7.9, pp D. Pucci, I. Aiello, A. Aprea, A. Bellusci, A. Crispini and M. Ghedini, Chem. Commun., 2009, 1550; D. Pucci, A. Crispini, M. Ghedini, E. I. Szerb, M. La Deda, Dalton Trans., 2011, 40, June 2013, Milan, Italy 12

21 Crystal Engineering of Pharmaceutical Co-crystals V. Ferretti Department of Chemical and Pharmaceutical Sciences and Centre for Structural Diffractometry, University of Ferrara, via L. Borsari 46, I Ferrara, Italy In the last years, the design and synthesis of co-crystals containing active pharmaceutical ingredients (APIs) has become the new frontier of the crystal engineering due to the great opportunity to modify the physico-chemical properties of solid forms of drugs. Actually, the pharmaceutical co-crystals display intermolecular motifs and hence crystal structure different from the pure API component, and consequently can exhibit diverse specific physical properties, such as solubility and dissolution rate; this makes it possible to hypothesize interesting influences in the bioavailability or local delivery of the drug itself. An efficient preparation of desired cocrystals requires an understanding and exploitation of the intermolecular interactions which may occur between the API and the other crystal co-formers in order to obtain robust supramolecular synthons. Relying on our long experience in the study of intermolecular interactions (in particular hydrogen bonding) and of co-crystals in general, we have started a project of supramolecular synthesis using different APIs and aromatic bases. In this communication the focus will be on cocrystals containing phloroglucinol (an example is shown in Fig.1), an antispasmodic agent, carbamazepine, an anticonvulsant, and indomethacin, a nonsteroidal anti-inflammatory drug. Besides a detailed investigation of the characteristic behaviour of the coformers functional groups (mostly hydrogen bonding donors or acceptors) and their influence on the crystal structures and packing motifs, the solubility and dissolution rate of some indomethacin cocrystals have been evaluated. Figure 1: The hydrogen bonding pattern for phloroglucinol/tetramethyl-pyrazine co-crystal. 6-7 June 2013, Milan, Italy 13

22 6-7 June 2013, Milan, Italy 14

23 SESSION II Chairman: Giuseppe Resnati 6-7 June 2013, Milan, Italy 15

24 Smart(ly Designed) Materials M. J. Zaworotko 1 1 University of South Floruida, Tampa, USA That composition and structure profoundly impact the properties of crystalline solids has provided impetus for exponential growth in the field of crystal engineering [1]. Strategies for the generation two classes of multi-component crystalline materials will be addressed: Pharmaceutical cocrystals [2] have emerged at the preformulation stage of drug development because their modular and designable nature facilitates discovery of new crystal forms of active pharmaceutical ingredients with changed physicochemical properties. We shall address the profound impact that cocrystallization can have upon solubility and bioavailability by presenting a case study. Metal-Organic Materials (MOMs) that are built from metal or metal cluster nodes and organic linkers have captured the imagination of materials scientists because they are amenable to crystal engineering and they offer unprecedented levels of porosity. Two families of MOMs are currently of interest to our group: in the context of gas storage and catalysis [3]. Pillared grids (see Figure 1) afford unprecedented selectivity for carbon capture in narrow pore MOMs [4]. In summary, this lecture will emphasize how crystal engineering has reached the end of the beginning, a rather exciting point in time since crystal engineering offers a paradigm shift from the more random, high-throughput methods that have traditionally been utilized in materials discovery and development. Figure 1: A schematic representation of a pillared grid framework (reference 4) References 1. (a) G.R. Desiraju, Crystal engineering: The design of organic solids Elsevier, 1989; (b) B. Moulton, M.J. Zaworotko, Chemical Reviews 2001, 101, P. Vishweshwar, J.A. McMahon, J.A. Bis, M.J. Zaworotko, J. Pharm. Sci. 2006, 95, Z.Z. Zhang, L. Zhang, L. Wojtas, P. Nugent, M. Eddaoudi, M.J. Zaworotko, J. Amer. Chem. Soc. 2012, 134, (a) S.D. Burd, S. Ma, J.A. Perman, B.J. Sikora, R.Q. Snurr, P.K. Thallapally, J. Tian, L. Wojtas, M.J. Zaworotko, J. Amer. Chem. Soc. 2012, 134, (b) M. Mohamed, S. Elsaidi, J. Wojtas, T. Pham, K.A. Forrest, B. Tudor, B. Space, M.J. Zaworotko, J. Amer. Chem. Soc., 2012, 134, (c) P. Nugent, Y. Belmabkhout, S.D. Burd, A.J. Cairns, R. Luebke, K.A. Forrest, T. Pham, S Ma, B. Space, L. Wojtas, M. Eddaoudi, M.J. Zaworotko, Nature, 2013, 495, June 2013, Milan, Italy 16

25 Intermolecular interactions in molecule-based magnets: Long-distance bonds between radical-ions M. Fumanal, a M. Capdevila, a J. S. Miller, b J. J. Novoa a a Dept. Química Física & IQTCUB, Fac. Química, Univ. Barcelona Av. Diagonal, 645, Barcelona (Spain) b Department of Chemistry, University of Utah, Salt Lake City, UT , USA Molecule-based crystals presenting magnetic properties show a rich polymorphism whose magnetostructural properties are not yet fully understood. A key factor for such limitation is the lack of a proper understanding of the energetic and magnetic properties of the radical radical interactions due to their combined bonding-electrostatic-dispersive character. This situation is particularly true when the molecule-based magnet presents radical-ions, in their structure. In some of these molecule-based magnets presenting radical-ions, the magnetic properties can only be explained by considering the formation of diamagnetic radical-ion radical-ion pairs. Despite the large separation of the radicals in these pairs, ~3 Å or larger, these pairs share most of the properties of covalent bonds, except their intrinsic stability (in most cases, they are metastable). However, these radical-ions pairs become energetically stable in room temperature solids, due to the combined effect of the radical-ion counterion interactions. They are also stable in various solutions, up to about -40 ºC, due to the combined impact of the radical-ion solvent interactions. This allows to talk about the presence of long, multicenter bonds between these radicals. 1,2 In this work we present the theoretical and experimental evidence concerning these bonds in pairs of radical-anions, radical-cations, and neutral radicals pairs. They are also found in radicalcation radical-anion pairs. Recent experimental results concerning the presence of these dimers in room temperature solution are also analyzed. References 1. (a) Novoa, J. J.; Lafuente, P.; Del Sesto, R. E.; Miller, J. S. Angew. Chem. Int. Ed. 2001, 40, 2540; (b) Del Sesto, R. E.; Miller, J. S.; Lafuente, P.; Novoa, J. J. Chem. Eur. J. 2002, 8, 4894; (c) Novoa, J. J.; Lafuente, P.; Del Sesto, R. E.; Miller, J. S. CrystEngComm 2002, 4, Miller, J. S.; Novoa, J. J. Acc. Chem. Res. 2007, 40, June 2013, Milan, Italy 17

26 Organic macrocycles for designing porous materials C. Tedesco 1 Dipartimento di Chimica e Biologia, Università degli Studi di Salerno,Fisciano (SA), Italy The development of self-assembled solid-state supramolecular architectures with nanosized pores or cavities is an intensively active research area, aiming at the preparation of new materials with potential applications in nanotechnology such as molecular sieves, sensors, and gas-storage devices. Organic solids could represent a competing alternative to zeolites, clays, metal-organic frameworks, mesoporous metal oxides. They feature not only the required porosity but also high selectivity, which can be achieved both by tailoring channel dimensions to guest molecules, and also by providing specific interactions with organic functional groups. Moreover, dynamic structural transformations based on flexible porous frameworks are always possible leading to functional materials with the fabrication of switches or actuators at a supramolecular level. Two types of macrocycles will be considered, namely calixarenes and cyclopeptoids. Both represent a class of very versatile compounds, which can be easily modified to achieve the desired building blocks. While cyclopeptoids constitute a class of relatively new compounds, whose properties are still unexplored [1,2], calixarenes have been successfully employed to obtain porous nanostructured materials.[3-8] Examples of the solid state assembly of both class of compounds will be reported to show their extreme versatility as building blocks for designing new materials. Figure 1: Two sodium ions and one cyclopeptoid molecule are linked to form a 1D polymer structure. References 1. N. Maulucci, I. Izzo, G. Bifulco, A. Aliberti, C. De Cola, D. Comegna, C. Gaeta, A. Napolitano, C. Pizza, C. Tedesco, D. Flot, F. De Riccardis, ChemComm. 2008, I. Izzo, G. Ianniello, C. De Cola, B. Nardone, L. Erra, G. Vaughan, C. Tedesco, F. De Riccardis, Org. Lett. 2013, 15, C. Tedesco, I. Immediata, L. Gregoli, L. Vitagliano, A. Immirzi, P. Neri, CrystEngComm 2005, 7, P. K. Thallapally, B. P. McGrail, J. L. Atwood, C. Gaeta, C. Tedesco, P. Neri, Chem. Mater. 2007, 19, C. Tedesco, L. Erra, M. Brunelli, V. Cipolletti, C. Gaeta, A. N. Fitch, J. L. Atwood, P. Neri, Chem. Eur. J. 2010, 42, L. Erra, C. Tedesco, V. R. Cipolletti, L. Annunziata, C. Gaeta, M. Brunelli, A. N. Fitch, C. Knöfel, P.L. Llewellyn, J. L. Atwood, P. Neri, Phys. Chem. Chem. Phys. 2012, 14, C. Tedesco, L. Erra, I. Immediata, C. Gaeta, M. Brunelli, M. Merlini, C. Meneghini, P. Pattison, P. Neri, Cryst. Growth Des. 2010, 10, L. Erra, C. Tedesco, I. Immediata, L. Gregoli, C. Gaeta, M. Merlini, C. Meneghini, M. Brunelli, A. N. Fitch, P. Neri, Langmuir 2012, 28, June 2013, Milan, Italy 18

27 SESSION III Chairman: Mir Wais Hosseini 6-7 June 2013, Milan, Italy 19

28 Crystallography of Large Supramolecular Complexes K. Rissanen Department of Chemistry, Nanoscience Center, University of Jyväskylä, JYU Jyväskylä, Finland An exciting research challenge in supramolecular chemistry is to design, synthesize, and characterize nano-sized architectures with applications in biology, chemistry, and materials science.[1] Predicting and designing non-covalently bound supramolecular complexes and assemblies is difficult because of the weakness of the interactions involved, thus the resulting superstructure is often a compromise between the geometrical constraints of the building blocks and the competing weak intermolecular interactions.[2] Our research interest has been focused on the studies of weak non-covalent intermolecular, viz. supramolecular interactions as the driving force in self-assembly and molecular recognition, especially in the solid state by single crystal X-ray diffraction. The most recent studies have focused on hydrogen[3] and halogen[4] bonded systems, i-i [5], CH anion [6], and anion i[7] interactions and metal ion coordination[8] in molecular self-assembly and molecular recognition in various systems such a resorcinarenes, ditopic receptors, rotaxanes, M 4 L 6 tetrahedra, M 8 L 6 cube, spheres, knots, etc.. The lecture will highlight some crystallographic studies of large (FW > 5000) supramolecular complexes. Fig. 1. The X-ray structure of the pentafoil knot. [8b] References 1. F. Hof, L.S. Craig, C. Nuckolls, J. Rebek Jr, Angew. Chem. Int. Ed. 2002, a) G.R. Desiraju Nature, 2001, b) T. Steiner, Angew. Chem. Int. Ed. 2002, N. Kodiah Beyeh, M. Cetina, K. Rissanen, Cryst. Growth Des. 2012, a) K. Raatikainen, K. Rissanen, Chem. Sci. 2 (2012), b) K. Raatikainen, K. Rissanen, CrystEngComm 2011, c) P. Metrangolo, Y. Carcenac, M. Lahtinen, T. Pilati, K. Rissanen, A. Vij, G. Resnati, Science 2009, a) H. Mansikkamäki, M. Nissinen, K. Rissanen, Angew. Chem. 2004, b) H. Mansikkamäki, S. Busi, M. Nissinen, A. Åhman, K. Rissanen, Chem. Eur. J. 2006, S.S. Zhu, H. Staats, K. Brandhorst, J. Grunenberg, F. Gruppi, E. Dalcanale, A. Lützen, K. Rissanen, C.A. Schalley, Angew. Chem. Int Ed. 2008, a) M. Giese, M. Albrecht, T. Krappitz, M. Peters, V. Gossen, G. Raabe, A. Valkonen, K. Rissanen, Chem. Comm. 48 (2012), b) M. Albrecht, C. Wessel, M. de Groot, K. Rissanen, A. Lüchow A, J. Am. Chem. Soc. 2008, J. Bunzen, J. Iwasa, P. Bonakdarzadeh, E. Numase, K. Rissanen, S. Sato, M. Fujita, Angew. Chem. 2012, b) J.-F. Ayme, J. E. Beves, D. A. Leigh, R. T. McBurney, K. Rissanen, D. Schultz, Nat. Chem. 2012, c) W. Meng, B. Breiner, K. Rissanen, J. D. Thoburn, J. K. Clegg, J. R. Nitschke, Angew. Chem. 2011, d) P. Mal, B. Breiner, K. Rissanen, J. R. Nitschke, Science 2009, June 2013, Milan, Italy 20

29 Crystallography And Supramolecular Sensing C. Massera, E. Biavardi, R. Pinalli, F. Ugozzoli, E. Dalcanale Dipartimento di Chimica, Parco Area delle Scienze 17/A, Italy The demand for fast and reliable detection of biological and chemical hazards as well as rapid and accurate diagnosis of diseases is continuously rising because of their foremost relevance in global health. Optimal sensors for environmental, security and biomedical applications must be sufficiently responsive to allow detection of the target analyte at low concentrations, and selective enough to respond primarily to a single chemical species in presence of interferents. In this respect resorcinarene-based cavitands, synthetic organic compounds with enforced cavities of molecular dimensions, represent a very important class of receptors for chemical and biochemical sensing [1]. In the design of cavitands, the choice of the bridging groups connecting the phenolic hydroxyls of the resorcinarene scaffold is pivotal, since it determines shape, dimensions and complexation properties of the resulting cavity. In this way the molecular recognition approach can be implemented using ad hoc synergic host-guest interactions to achieve the desired selectivity towards different types of analytes [2, 3]. In the case of aromatic guests, quinoxaline-bridged (QxCav) and linked quinoxaline-bridged (QxBox) cavitands have proved to be extremely effective receptors through the formation of - stacking and CH- interactions (Figure 1). Figure 1: Molecular structure of the complex formed between the cavitand QxBox and benzene. In this framework, single-crystal X-ray analysis on the resulting complexes is an extremely important diagnostic tool because it provides precise information on the type, number, strength and geometry of the weak interactions responsible for host-guest association in the solid state, allowing to predict the sensor behavior. References 1. D. J. Cram, Science, 1983, 219, R. Pinalli, M. Suman, E. Dalcanale, Eur. J. Org. Chem., 2004, L. Pirondini, E. Dalcanale, Chem. Soc. Rev., 2007, 36, June 2013, Milan, Italy 21

30 Network Analysis in Crystal Engineering, More than a Dull Taxonomy Exercise L. Öhrström 1 1 Chalmers Tekniska Högskola, Dept. of Chemical and Biological Engineering, Göteborg, Sweden At a first glance, analysis of network topologies, [1] deals with chemical objects that have already been created and might thus superficially be dismissed as nomenclature exercises of little value to the creative chemist. However, rejecting this as mere workout in taxonomy is completely wrong, as opportunities of a deeper understanding and of an efficient presentation may be lost in the process. Moreover, this approach also has a forward looking component, enabling us to design solid state molecule-based materials, thus to do crystal engineering. There are four important reasons for finding out the network topology of a crystal structure, be this a Metal-Organic Framework, Coordination Polymer or a hydrogen bonded system: 1. To understand the products we have. 2. To compare these materials to what others have made. 3. To efficiently communicate our results to colleagues. 4. To truly make something new by design. That the method is widely applicable is illustrated below by the new tetragonal allotrope of the group 14 elements, the T12 phase. [2] This allotrope was proposed based on elaborate computational methods, accounting for some experimental results in synthesized metastable phases but could easily have been predicted by the analysis of network topologies with appropriate geometrical constraints. [3] Figure 1. The Si T12 phase (left, Reprinted with permission from Zhao, Z.; Tian, F.; Dong, X.; Li, Q.; Wang, Q.; Wang, H.; Zhong, X.; Xu, B.; Yu, D.; He, J.; Wang, H.-T.; Ma, Y.; Tian, Y. J. Am. Chem. Soc. 2012, 134, (2012) the American Chemical Society) and the ideal cdp net from the RCSR database. 1. A. F. Wells, Acta Cryst. 1954, 7, Z. Zhao, F. Tian, X. Dong, Q. Li, Q. Wang, H. Wang, X. Zhong, B. Xu, D. Yu, J. He, H.-T. Wang, Y. Ma, Y. Tian, J. Am. Chem. Soc. 2012, 134, L. Öhrström, M. O'Keeffe, Z. Kristallogr. in press June 2013, Milan, Italy 22

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