From Frustrated Packing to Tecton-Driven Porous Molecular Solids

被引:8
作者
Gunawardana, Chamara A. [1 ]
Sinha, Abhijeet S. [1 ]
Reinheimer, Eric W. [2 ]
Aakeroy, Christer B. [1 ]
机构
[1] Kansas State Univ, Dept Chem, Manhattan, KS 66506 USA
[2] Americas Corp, 9009 New Trails Dr, The Woodlands, TX 77381 USA
来源
CHEMISTRY-SWITZERLAND | 2020年 / 2卷 / 01期
关键词
crystal engineering; porous material; molecular recognition; halogen bond; co-crystal; molecular tecton; binary solid; network structure; sigma-hole; molecular electrostatic potential; CRYSTAL-STRUCTURES; ORGANIC-MOLECULES; DIAMONDOID NETS; C-H; HALOGEN; ETHYNYLBENZENE; FRAMEWORKS; STORAGE;
D O I
10.3390/chemistry2010011
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Structurally divergent molecules containing bulky substituents tend to produce porous materials via frustrated packing. Two rigid tetrahedral cores, tetraphenylmethane and 1,3,5,7-tetraphenyladamantane, grafted peripherally with four (trimethylsilyl)ethynyl moieties, were found to have only isolated voids in their crystal structures. Hence, they were modified into tecton-like entities, tetrakis(4-(iodoethynyl)phenyl)methane [I4TEPM] and 1,3,5,7-tetrakis(4-(iodoethynyl)phenyl)adamantane [I(4)TEPA], in order to deliberately use the motif-forming characteristics of iodoethynyl units to enhance crystal porosity. I4TEPM not only holds increased free volume compared to its precursor, but also forms one-dimensional channels. Furthermore, it readily co-crystallizes with Lewis basic solvents to afford two-component porous crystals.
引用
收藏
页码:179 / 192
页数:14
相关论文
共 56 条
[1]   Supramolecular Hierarchy among Halogen-Bond Donors [J].
Aakeroey, Christer B. ;
Baldrighi, Michele ;
Desper, John ;
Metrangolo, Pierangelo ;
Resnati, Giuseppe .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (48) :16240-16247
[2]   PHOSPHONITRILIC COMPOUNDS .3. MOLECULAR INCLUSION COMPOUNDS OF TRIS(O-PHENYLENEDIOXY)PHOSPHONITRILE TRIMER [J].
ALLCOCK, HR ;
SIEGEL, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (23) :5140-&
[3]   Polymorphs and co-crystals of haloprogin: an antifungal agent [J].
Baldrighi, Michele ;
Bartesaghi, Davide ;
Cavallo, Gabriella ;
Chierotti, Michele R. ;
Gobetto, Roberto ;
Metrangolo, Pierangelo ;
Pilati, Tullio ;
Resnati, Giuseppe ;
Terraneo, Giancarlo .
CRYSTENGCOMM, 2014, 16 (26) :5897-5904
[4]   Crystal porosity and the burden of proof [J].
Barbour, LJ .
CHEMICAL COMMUNICATIONS, 2006, (11) :1163-1168
[5]   DIANINS COMPOUND AS A ZEOLITIC SORBENT [J].
BARRER, RM ;
SHANSON, VH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (09) :333-334
[6]   Thermally robust and porous noncovalent organic framework with high affinity for fluorocarbons and CFCs [J].
Chen, Teng-Hao ;
Popov, Ilya ;
Kaveevivitchai, Watchareeya ;
Chuang, Yu-Chun ;
Chen, Yu-Sheng ;
Daugulis, Olafs ;
Jacobson, Allan J. ;
Miljanic, Ognjen S. .
NATURE COMMUNICATIONS, 2014, 5
[7]   Molecular tectonics.: Porous hydrogen-bonded networks built from derivatives of 2,2′,7,7'-Tetraphenyl-9,9′-spirobi[9H-fluorene] [J].
Demers, E ;
Maris, T ;
Wuest, JD .
CRYSTAL GROWTH & DESIGN, 2005, 5 (03) :1227-1235
[8]   Structural Variability in the Monofluoroethynylbenzenes Mediated through Interactions Involving "Organic" Fluorine [J].
Dikundwar, Amol G. ;
Sathishkumar, Ranganathan ;
Row, Tayur N. Guru ;
Desiraju, Gautam R. .
CRYSTAL GROWTH & DESIGN, 2011, 11 (09) :3954-3963
[9]   OLEX2: a complete structure solution, refinement and analysis program [J].
Dolomanov, Oleg V. ;
Bourhis, Luc J. ;
Gildea, Richard J. ;
Howard, Judith A. K. ;
Puschmann, Horst .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341
[10]   CRYSTAL-STRUCTURE OF DIIODACETYLENE - EXAMPLE OF PSEUDOSYMMETRY [J].
DUNITZ, JD ;
BRITTON, D ;
GEHRER, H .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1972, B 28 (JUL15) :1989-&