Crystal structures of resorcin[4]arene and pyrogallol[4]arene complexes with DL-pipecolinic acid. Model compounds for the recognition of the pipecolinyl ring, a key fragment of FK506, through C–H⋯π interaction

Fujisawa, Ikuhide; Kitamura, Yuji; Kato, Ryo; Murayama, Kazutaka; Aoki, Katsuyuki

doi:10.1016/j.molstruc.2013.10.026

Cited by 14 publications

(9 citation statements)

References 37 publications

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“…The bowl‐shaped cavity of the RsC and PgC also works as perfect host for guest molecules of different shapes and functionalities . These structural features are useful not only in the construction of various supramolecular frameworks, such as hydrogen‐bonded dimers/hexamers and metal‐seamed dimers/hexamers, but also in the applications of RsC and PgC in the field of, for example, molecular recognition, host–guest complexes, gas sorption and separation …”

Section: Methodsmentioning

confidence: 99%

Process Development for Separation of Conformers from Derivatives of Resorcin[4]arenes and Pyrogallol[4]arenes

Patil

Zhang

Atwood

2016

Chemistry A European J

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Macrocyclic compounds, such as resorcin[4]arenes and pyrogallol[4]arenes, have proven to be useful building blocks in the construction of supramolecular organic frameworks (SOFs) because of their unique bowl-like shape and ability to interact through variety of intermolecular interactions. Herein, we report the synthesis and crystal structures of two functionalized resorcin[4]arenes and pyroagllol[4]arenes, 4-hydroxyphenylresorcin[4]arenes, and 4-hydroxyphenylpyrogallol[4]arenes. These phenyl-functionalized macrocycles usually have different conformers, such as cone, boat, chair, saddle, and diamond. The successful separation of predominant conformers from the crude product was carried out with solvent-extraction technique. The shape and molecular arrangement of these conformers in the individual crystal structure was verified with single-crystal X-ray diffraction studies.

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Section: Methodsmentioning

confidence: 99%

Process Development for Separation of Conformers from Derivatives of Resorcin[4]arenes and Pyrogallol[4]arenes

Patil

Zhang

Atwood

2016

Chemistry A European J

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“…17,18 These SOFs of RsCs and PgCs have also been characterized to understand host−guest interactions 19,20 and molecular recognition. 21,22 These SOFs often enclosed void spaces and channels within the extended crystal structure, which are filled with disordered solvent molecules. 15,23 To expand the class of SOFs based on calixarenes, here we report synthesis of two novel SOFs using a large macrocycle, noria (C 102 H 96 O 24 ), and 4,4′-bipyridine (bpy) or 1,2-bis(4-pyridyl)ethylene (bpe) as building blocks (Figure 1A).…”

Section: ■ Introductionmentioning

confidence: 99%

Construction of Supramolecular Organic Frameworks Based on Noria and Bipyridine Type Spacers

Patil

Zhang

Barnes

et al. 2016

Crystal Growth & Design

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Among the class of porous crystalline materials, supramolecular organic frameworks (SOFs) have proven to be of great importance due to their potential applications in gas sorption/separation, catalysis, and nanotechnology. Herein, we present construction and characterization of two novel SOFs based on a large macrocyclic compound, noria, and linker molecules such as 4,4′-bypyridine and 1,2-bis(4-pyridyl)ethylene. Use of bipyridine type spacer molecules can partially or completely replace typical O–H···O intermolecular hydrogen bonds between noria molecules by O–H···N interactions. Due to the moderate length difference, the two spacer molecules lead to the assembly of 1D chains and 2D networks, respectively.

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“…Recently, the Atwood group reported that coordination polymers can be formed using pyrogallol[4]arene-based metal organic nanocapsules (MONCs) as secondary building units. Pyrogallol[4]arenes (PgCs) are calixarene-like macrocyclic molecules that are used primarily as supramolecular building blocks in materials constructed through noncovalent means. − However, with an upper rim consisting of 12 phenolic hydroxyl groups, these macrocycles can also function as coordinative building blocks in the construction of more complex superstructures. Common structural motifs of PgC-based entities include the hexameric (PgC) 6 M 24 and dimeric (PgC) 2 M 8 MONCs formed with transition metal cations − and the infinite-layered networks formed with alkali cations, , among others. , The cage-like coordination complexes formed from transition metal cations are very similar in size and shape to their noncovalently seamed complementary supramolecules , and feature two distinct coordination patterns: eight distinct trimetal clusters in the hexamer and an “octametal belt” in the dimer. ,− , The coordination number of the metal cations is also different in the two motifs, with tetra- or hexacoordinate sites seen in the hexamer and pentacoordinate sites typically seen in the dimer.…”

Section: Introductionmentioning

confidence: 99%

Metal Organic Nanocapsules as Two-Dimensional Network Building Blocks

et al. 2016

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Metal−organic frameworks (MOFs) are a class of porous materials with a wide variety of applications, including molecular adsorption and separation. Recently, the first MOF based on the zincseamed pyrogallol[4]arene nanocapsule as a secondary building unit was reported. The zinc-seamed nanocapsules are linked together with 4,4′bipyridine, which is a divergent ligand commonly used in the synthesis of MOFs. In an effort to identify other likely candidates for nanocapsular linking, electronic structure calculations were performed to determine energetic and geometric properties of (Zn(C 2 O 2 H 3 ) 2 ) 1,2 Y model complexes, which have been shown previously to reliably model the zinc coordination sphere found in the nanocapsules. Here, Y represents one of 17 divergent ligands with N, S, or O electron-donating atoms. MOFs were synthesized and characterized from two of the ligands suggested as most suitable for further experimental study.

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Crystal structures of resorcin[4]arene and pyrogallol[4]arene complexes with DL-pipecolinic acid. Model compounds for the recognition of the pipecolinyl ring, a key fragment of FK506, through C–H⋯π interaction

Cited by 14 publications

References 37 publications

Process Development for Separation of Conformers from Derivatives of Resorcin[4]arenes and Pyrogallol[4]arenes

Process Development for Separation of Conformers from Derivatives of Resorcin[4]arenes and Pyrogallol[4]arenes

Construction of Supramolecular Organic Frameworks Based on Noria and Bipyridine Type Spacers

Metal Organic Nanocapsules as Two-Dimensional Network Building Blocks

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