Recent Developments in Crystal Engineering

In recent years, Asian countries, especially China and India, are making significant progress in the field of crystal engineering. The recent surge of publications in this area from these countries in high impact journals is a tangible measure of this activity. An important milestone in this direction was the China−India−Singapore Symposium on Crystal Engineering recently held at the National University of Singapore. This symposium brought researchers working in this field to meet, discuss, present, and exchange their research work and has generated momentum to further accelerate the growth of this field. This perspective highlights the recent advances discussed by the researchers at this symposium in the fast growing field of crystal engineering.

[1]  Shoutian Zheng,et al.  Designed synthesis of POM-organic frameworks from {Ni6PW9} building blocks under hydrothermal conditions. , 2008, Angewandte Chemie.

[2]  Xin-Xiong Li,et al.  Cubic polyoxometalate-organic molecular cage. , 2010, Journal of the American Chemical Society.

[3]  R. Tan,et al.  Dimorphs of a 1 : 1 cocrystal of ethenzamide and saccharin: solid-state grinding methods result in metastable polymorph , 2009 .

[4]  Ming Wah Wong,et al.  Structure of 4,4-Bisphenylsulfonyl-N,N-dimethylbutylamine: Interplay of Intramolecular C–H···N, C–H···O=S, and ?···? Interactions , 2009 .

[5]  Y. Tong,et al.  Assembly of CdI2-type coordination networks from triangular ligand and octahedral metal center: topological analysis and potential framework porosity. , 2008, Chemical communications.

[6]  C. Su,et al.  Temperature-dependent guest-driven single-crystal-to-single-crystal ligand exchange in a two-fold interpenetrated Cd(II) grid network. , 2009, Chemistry.

[7]  S. Verma,et al.  A luminescent silver-adenine metallamacrocyclic quartet. , 2006, Journal of the American Chemical Society.

[8]  Gautam R. Desiraju,et al.  Long-range synthon Aufbau modules (LSAM) in crystal structures: systematic changes in C6H6−nFn (0 ≤ n ≤ 6) fluorobenzenes , 2010 .

[9]  Shoutian Zheng,et al.  Combination between lacunary polyoxometalates and high-nuclear transition metal clusters under hydrothermal conditions: I. from isolated cluster to 1-D chain. , 2007, Chemical communications.

[10]  X. Bu,et al.  Two unprecedented 10-connected bct topological metal-organic frameworks constructed from cadmium clusters. , 2010, Chemical communications.

[11]  C. Su,et al.  Thermally stable porous hydrogen-bonded coordination networks displaying dual properties of robustness and dynamics upon guest uptake. , 2010, Chemistry.

[12]  Susumu Kitagawa,et al.  Functional porous coordination polymers. , 2004, Angewandte Chemie.

[13]  Junwei Zhao,et al.  A combination of lacunary polyoxometalates and high-nuclear transition-metal clusters under hydrothermal conditions. Part II: From double cluster, dimer, and tetramer to three-dimensional frameworks. , 2007, Chemistry.

[14]  K. Biradha,et al.  Two-Dimensional Organic Brick-Wall Layers as Hosts for the Inclusion and Study of Aromatics Ensembles: Acid−Pyridine and Acid−Carbonyl Synthons for Multicomponent Materials , 2009 .

[15]  J. Bai,et al.  A new kind CO2/CH4 separation material: open ended nitrogen doped carbon nanotubes formed by direct pyrolysis of metal organic frameworks. , 2010, Chemical communications.

[16]  X. Bu,et al.  An azido-metal-isonicotinate complex showing long-range ordered ferromagnetic interaction: synthesis, structure and magnetic properties. , 2006, Chemical communications.

[17]  K. A. Padmanabhan,et al.  Structure−Property Correlations in Bending and Brittle Organic Crystals , 2006 .

[18]  R. Banerjee,et al.  Selective CO2 and H2 adsorption in a chiral magnesium-based metal organic framework (Mg-MOF) with open metal sites , 2010 .

[19]  J. Baruah,et al.  Coordination polymers of zinc with 2,2'-(2,3-bis-phenylsulfanylnaphthalene-1,4-yloxy)diacetic acid. , 2009, Dalton transactions.

[20]  A. Ramanan,et al.  Understanding Supramolecular Interactions Provides Clues for Building Molecules into Minerals and Materials: a Retrosynthetic Analysis of Copper-Based Solids , 2010 .

[21]  C. Su,et al.  An unusual 3D coordination polymer assembled through parallel interpenetrating and polycatenating of (6,3) nets , 2009 .

[22]  Hao,et al.  Local similarity in organic crystals and the non-uniqueness of X-ray powder patterns. , 1999, Acta crystallographica. Section B, Structural science.

[23]  S. Patil,et al.  Diketopyrrolopyrrole-Based Donor-Acceptor Copolymers as Organic Sensitizers for Dye Sensitized Solar Cells , 2010 .

[24]  J. Vittal,et al.  First examples of Au(I)-X-Ag(I) halonium cations (X = Cl and Br). , 2003, Journal of the American Chemical Society.

[25]  H. Su,et al.  Crystallographic evidence of an unusual, pentagon-shaped folding pattern in a circular aromatic pentamer. , 2008, Organic letters.

[26]  X. Bu,et al.  Partial substitution of hydroxyl by azide: an unprecedented 2D azido-copper-hydroxyl compound with a [Cu(24)] macrocycle in the presence of [Cu(H2O)6]2+. , 2008, Chemistry.

[27]  Michael O'Keeffe,et al.  Designed Synthesis of 3D Covalent Organic Frameworks , 2007, Science.

[28]  Quan‐Ming Wang,et al.  A facile template approach to high-nuclearity silver(I) alkynyl clusters. , 2009, Angewandte Chemie.

[29]  Y. Tong,et al.  Discrete Chiral Single-Crystal Microtubes Assembled with Honeycomb Coordination Networks Showing Structural Diversity and Borromean Topology in One Single Crystal , 2007 .

[30]  R. Banerjee,et al.  Synthesis and structural comparisons of five new fluorinated metal organic frameworks (F-MOFs) , 2010 .

[31]  H. Su,et al.  Persistently folded circular aromatic amide pentamers containing modularly tunable cation-binding cavities with high ion selectivity. , 2010, Journal of the American Chemical Society.

[32]  Xiao-Ming Chen,et al.  Exceptional framework flexibility and sorption behavior of a multifunctional porous cuprous triazolate framework. , 2008, Journal of the American Chemical Society.

[33]  H. Su,et al.  Helical organization in foldable aromatic oligoamides by a continuous hydrogen-bonding network. , 2009, Organic letters.

[34]  C. Su,et al.  Dimension Increase via Hydrogen Bonding and Weak Coordination Interactions from Simple Complexes of 2-(Pyridyl)benzimidazole Ligands , 2007 .

[35]  S. Verma,et al.  Decanuclear copper framework supported by a tripodal adenine ligand. , 2010, Inorganic chemistry.

[36]  Gautam R Desiraju,et al.  C-H...O and other weak hydrogen bonds. From crystal engineering to virtual screening. , 2005, Chemical communications.

[37]  J. Baruah,et al.  Different solvates of two isomeric dicarboxylic acids with pyridine and quinoline , 2009 .

[38]  M. Jaskólski,et al.  Isostructurality in crystalline oxa-androgens: a case of C–O–H···O and C–H···O interaction mimicry and solid solution formation , 1998 .

[39]  J. Vittal,et al.  Coordination Polymers Versus Metal−Organic Frameworks , 2009 .

[40]  M. Du,et al.  A 3D copper(II) coordination framework showing different kinetic and thermodynamic crystal transformations through removal of guest water cubes. , 2009, Chemistry.

[41]  K. Biradha,et al.  Stepwise dimerization of double [2 + 2] reaction in the co-crystals of 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one and phloroglucinol: a single-crystal to single-crystal transformation , 2008 .

[42]  Wenchuan Wang,et al.  Targeted synthesis of a porous aromatic framework with high stability and exceptionally high surface area. , 2009, Angewandte Chemie.

[43]  T. Row,et al.  Evaluation of the interchangeability of C–H and C–F groups: insights from crystal packing in a series of isomeric fluorinated benzanilides , 2008 .

[44]  Yan‐Qiong Sun,et al.  Porous lanthanide-organic open frameworks with helical tubes constructed from interweaving triple-helical and double-helical chains. , 2005, Angewandte Chemie.

[45]  Wei‐Xiong Zhang,et al.  A "Star" antiferromagnet: a polymeric iron(III) acetate that exhibits both spin frustration and long-range magnetic ordering. , 2007, Angewandte Chemie.

[46]  K. Biradha,et al.  Carboxylic Acid and Phenolic Hydroxyl Interactions in the Crystal Structures of Co-Crystals/Clathrates of Trimesic Acid and Pyromellitic Acid with Phenolic Derivatives , 2010 .

[47]  A. Karmakar,et al.  Crystal packing in some flexible carboxylic acids and esters attached to a naphthalene ring , 2008 .

[48]  D. Braga.  Inorganic crystal engineering: a personal perspective , 2000 .

[49]  Pui Shan Chow,et al.  Trimorphs of a pharmaceutical cocrystal involving two active pharmaceutical ingredients: potential relevance to combination drugs , 2009 .

[50]  Gérard Férey,et al.  Hybrid porous solids: past, present, future. , 2008, Chemical Society reviews.

[51]  S. Kitagawa,et al.  Selective gas adsorption and unique structural topology of a highly stable guest-free zeolite-type MOF material with N-rich chiral open channels. , 2008, Chemistry.

[52]  G. Lu,et al.  Ammonia borane confined by a metal-organic framework for chemical hydrogen storage: enhancing kinetics and eliminating ammonia. , 2010, Journal of the American Chemical Society.

[53]  X. You,et al.  One-step solid-state thermolysis of a metal-organic framework: a simple and facile route to large-scale of multiwalled carbon nanotubes. , 2008, Chemical communications.

[54]  M. W. Wong,et al.  Saturated hydrocarbon-benzene complexes: theoretical study of cooperative CH/pi interactions. , 2006, The journal of physical chemistry. A.

[55]  Shoutian Zheng,et al.  Lanthanide-transition-metal sandwich framework comprising {Cu3} cluster pillars and layered networks of {Er36} wheels. , 2005, Angewandte Chemie.

[56]  K. Biradha,et al.  Design of Cocrystals via New and Robust Supramolecular Synthon between Carboxylic Acid and Secondary Amide: Honeycomb Network with Jailed Aromatics , 2009 .

[57]  K. Biradha,et al.  Crystal engineering with acid and pyridine heteromeric synthon: neutral and ionic co-crystals , 2008 .

[58]  Tejender S. Thakur,et al.  C–H⋯F–C hydrogen bonding in 1,2,3,5-tetrafluorobenzene and other fluoroaromatic compounds and the crystal structure of alloxan revisited , 2010 .

[59]  X. Bu,et al.  Structures with tunable strong ferromagnetic coupling: from unordered (1D) to ordered (Discrete). , 2007, Chemistry.

[60]  Gautam R. Desiraju,et al.  Molecular and crystal structure of 4-ethynylcyanobenzene. An example of CH⋯N hydrogen bonding , 2010 .

[61]  L. Long,et al.  Framework solids possessing both hydrophobic and hydrophilic pores constructed by face-sharing keplerate-type heterometal-organic polyhedra. , 2010, Chemistry.

[62]  R. Tan,et al.  Polymorphs and Solvates of a Cocrystal Involving an Analgesic Drug, Ethenzamide, and 3,5-Dinitrobenzoic Acid , 2010 .

[63]  Quan‐Ming Wang,et al.  Snowman-like silver alkynyl cluster consolidated by templating chloride and peripheral trifluoroacetates. , 2008, Chemical communications.

[64]  Quan‐Ming Wang,et al.  High-nuclearity silver clusters templated by carbonates generated from atmospheric carbon dioxide fixation. , 2009, Journal of the American Chemical Society.

[65]  Jishan Wu,et al.  Efficient synthesis of a hetero[4]rotaxane by a "threading-stoppering-followed-by-clipping" approach. , 2010, Organic & biomolecular chemistry.

[66]  Kian Ping Loh,et al.  The chemistry of graphene , 2010 .

[67]  C. Su,et al.  Two robust porous metal-organic frameworks sustained by distinct catenation: selective gas sorption and single-crystal-to-single-crystal guest exchange. , 2010, Chemistry, an Asian journal.

[68]  M. Tong,et al.  Coordination Chemistry of Cyclohexane-1,2,4,5-tetracarboxylate (H4L). Synthesis, Structure, and Magnetic Properties of Metal-Organic Frameworks with Conformation-Flexible H4L Ligand , 2009 .

[69]  Shoutian Zheng,et al.  Poly(polyoxotungstate)s with 20 nickel centers: from nanoclusters to one-dimensional chains. , 2009, Angewandte Chemie.

[70]  M. Du,et al.  Flexible Building Blocks of N,N‘-Bis(picolinoyl)hydrazine for Hydrogen-Bonding Directed Cocrystallization: Structural Diversity, Concomitant Polymorphs, and Synthon Prediction , 2006 .

[71]  E. Balaraman,et al.  Synthesis and utility of new amine/nucleobase addition products of allenylphosphonates , 2006 .

[72]  K. Biradha,et al.  Nitrate Ion Assisted Argentophilic Interactions as a Template for Solid State [2 + 2] Photodimerization of Pyridyl Acrylic Acid, Its Methyl Ester, and Acryl Amide , 2010 .

[73]  R. Banerjee,et al.  Structural, Magnetic, and Gas Adsorption Study of a Two-Dimensional Tetrazole-Pyrimidine Based Metal−Organic Framework , 2010 .

[74]  Changquan Calvin Sun.  Materials science tetrahedron--a useful tool for pharmaceutical research and development. , 2009, Journal of pharmaceutical sciences.

[75]  M. W. Wong,et al.  Structures and vibrational spectra of the sulfur-rich oxides SnO (n = 4-9): the importance of pi*-pi* interactions. , 2007, Chemistry.

[76]  C. Su,et al.  [Co2(ppca)2(H2O)(V4O12)0.5]: a framework material exhibiting reversible shrinkage and expansion through a single-crystal-to-single-crystal transformation involving a change in the cobalt coordination environment. , 2005, Angewandte Chemie.

[77]  M. Du,et al.  Co-crystallization of a versatile building block 4-amino- 3,5-bis(4-pyridyl)-1,2,4-triazole with R-isophthalic acids (R = –H, –NH2, –SO3H, and –COOH): polymorphism and substituent effect on structural diversity , 2009 .

[78]  Jie‐Peng Zhang,et al.  Optimized acetylene/carbon dioxide sorption in a dynamic porous crystal. , 2009, Journal of the American Chemical Society.

[79]  Seth M. Cohen,et al.  Postsynthetic modification of metal-organic frameworks. , 2009, Chemical Society reviews.

[80]  Shoutian Zheng,et al.  A germanate framework containing 24-ring channels, Ni--Ge bonds, and chiral [Ni@Ge14O24(OH)3] cluster motifs transferred from chiral metal complexes. , 2005, Angewandte Chemie.

[81]  C. Su,et al.  Zero to three dimensional increase of silver(I) coordination assemblies controlled by deprotonation of 1,3,5-tri(2-benzimidazolyl)benzene and aggregation of multinuclear building units. , 2007, Inorganic chemistry.

[82]  Satish Patil,et al.  Synthesis of diketopyrrolopyrrole containing copolymers: a study of their optical and photovoltaic properties. , 2010, The journal of physical chemistry. B.

[83]  D. Kuang,et al.  Self-assembly of 2D Borromean networks through hydrogen-bonding recognition. , 2009, Chemical communications.

[84]  Xiao-Ning Cheng,et al.  A Dynamic Porous Magnet Exhibiting Reversible Guest‐Induced Magnetic Behavior Modulation , 2007 .

[85]  J. Vittal.  Supramolecular structural transformations involving coordination polymers in the solid state , 2007 .

[86]  Jishan Wu,et al.  Synthesis of [n]rotaxanes by template-directed clipping: the role of the dialkylammonium recognition sites. , 2010, Organic letters.

[87]  R. Banerjee,et al.  Structural Diversity in Partially Fluorinated Metal Organic Frameworks (F-MOFs) Composed of Divalent Transition Metals, 1,10-Phenanthroline, and Fluorinated Carboxylic Acid , 2010 .

[88]  S. Verma,et al.  Patterned deposition of a mixed-coordination adenine-silver helicate, containing a pi-stacked metallacycle, on a graphite surface. , 2007, Journal of the American Chemical Society.

[89]  Bing Yuan,et al.  Microengineering of Supramolecular Soft Materials by Design of the Crystalline Fiber Networks , 2010 .

[90]  C. Su,et al.  Recent Advances in Supramolecular Design and Assembly of Silver(i) Coordination Polymers , 2006 .

[91]  J. Kumar,et al.  The many facets of adenine: coordination, crystal patterns, and catalysis. , 2010, Accounts of chemical research.

[92]  C. Su,et al.  Three-fold parallel interlocking of 2-D brick-wall networks showing ladder-like unsymmetrical Borromean links , 2006 .

[93]  Jishan Wu,et al.  Efficient preparation of separable pseudo[n]rotaxanes by selective threading of oligoalkylammonium salts with cucurbit[7]uril. , 2009, Chemistry.

[94]  Wei‐Yin Sun,et al.  Spontaneous resolution of two homochiral ferroelectric cadmium(II) frameworks and an achiral framework from a one-pot reaction involving achiral rigid ligands , 2010 .

[95]  K. Biradha,et al.  Assembling triple helical amide-to-amide hydrogen bonded columns of tris(4-halophenyl)benzene-1,3,5-tricarboxamides into porous materials via halogen...halogen interactions. , 2010, Chemical communications.

[96]  X. Bu,et al.  Three-Dimensional Homospin Inorganic–Organic Ferrimagnet Constructed from (VO3–)n Chains Linking {[5-(Pyrimidin-2-yl)tetrazolato-(CuII)1.5]2+}n Layers , 2008 .

[97]  L. Long,et al.  Keeping the ball rolling: fullerene-like molecular clusters. , 2010, Accounts of chemical research.

[98]  Michael J Zaworotko,et al.  Design and synthesis of metal-organic frameworks using metal-organic polyhedra as supermolecular building blocks. , 2009, Chemical Society reviews.

[99]  Kumar Biradha,et al.  Crystal engineering of coordination polymers using 4,4'-bipyridine as a bond between transition metal atoms. , 2006, Chemical communications.

[100]  Michael J. Zaworotko,et al.  Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? , 2004 .

[101]  H. Su,et al.  Synthesis, structural investigations, hydrogen-deuterium exchange studies, and molecular modeling of conformationally stablilized aromatic oligoamides. , 2010, Journal of the American Chemical Society.

[102]  Gautam R. Desiraju,et al.  Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis , 1995 .

[103]  X. Bu,et al.  Azido-mediated systems showing different magnetic behaviors. , 2009, Chemical Society reviews.

[104]  J. Kumar,et al.  Directing spatial disposition of ferrocene around homoadenine tetrads. , 2008, Chemical communications.

[105]  C. Su,et al.  Formation of two (6,3) networks showing structural diversity, Borromean topology and conformational chirality in the same crystal. , 2007, Chemical communications.

[106]  S. Ng,,et al.  Spin-frustrated complex, [Fe(II)Fe(III)(trans-1,4-cyclohexanedicarboxylate)1.5]infinity: interplay between single-chain magnetic behavior and magnetic ordering. , 2009, Inorganic chemistry.

[107]  J. Qiao,et al.  A giant silver alkynyl cage with sixty silver(I) ions clustered around polyoxometalate templates. , 2010, Angewandte Chemie.

[108]  Shoutian Zheng,et al.  Lanthanide germanate cluster organic frameworks constructed from {Ln(8)Ge(12)} or {Ln(11)Ge(12)} cage cluster building blocks. , 2009, Journal of the American Chemical Society.

[109]  P. Dastidar,et al.  Supramolecular gelling agents: can they be designed? , 2008, Chemical Society reviews.

[110]  Guo-Yu Yang,et al.  A 3D coordination framework based on linkages of nanosized hydroxo lanthanide clusters and copper centers by isonicotinate ligands. , 2005, Angewandte Chemie.

[111]  J. Vittal,et al.  Coordination polymers of d10 metals and N,N'-bis(3-pyridinecarboxamide)-1,2-ethane , 2001 .