Guest induced transformations of assembled pyridyl bis-urea macrocycles

Roy, Kinkini; Wang, Chun; Smith, Mark D.; Dewal, Mahender B.; Wibowo, Arief C.; Brown, Julius C.; Ma, Shuguo; Shimizu, Linda S.

doi:10.1039/c0cc01952f

Cited by 31 publications

(64 citation statements)

References 25 publications

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“…i) Carbon dioxide adsorption isotherms at 273 K for host 36 (adsorption in blue, desorption in red) and hydrogen adsorption isotherms at 273 K for host 36 (inset). Reproduced with permission . Copyright 2011, The Royal Society of Chemistry.…”

Section: Other Supramolecular‐macrocycle‐based Comsmentioning

confidence: 99%

“…A bis‐urea with pyridine linkers ( 36 ) also self‐assembled into columnar structures with high fidelity ( 36a ). However, a high density structure without obvious channels forms due to the close packing of these columns (Figure f) . In spite of the lack of pores, 36a was able to adsorb guests including trifluoroethanol and iodine due to their relatively strong interactions with 36 .…”

Section: Other Supramolecular‐macrocycle‐based Comsmentioning

confidence: 99%

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Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

et al. 2019

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macrocycles. They have been also employed to modify the surface properties of metal nanoparticles via noncovalent host−guest interactions, [31] covering their applications in drug delivery, [32] highly sensitive sensors, [33] selective catalysis, [34] and so on.In addition to their intensive applications based on their host−guest chemistry, macrocycles have also been used as building blocks to construct solid materials including porous organic polymers (POPs), [35,36] metal-organic frameworks (MOFs), [37][38][39][40][41][42][43] and crystalline organic materials (COMs). [44][45][46][47][48][49][50][51][52][53][54][55][56][57] Particular attention should be paid to COMs, a class of organic materials featuring facile preparation, high crystallinity, structural diversity, chemical stability, solution-processability, etc. [58][59][60][61][62][63][64][65][66][67][68][69][70] Different from MOFs that are composed of both inorganic (metal ions) and organic species (organic ligands) through coordination, COMs refer to a kind of crystalline materials composed of pure organics connected by either covalent or noncovalent bonds. [71][72][73] For COMs connected by noncovalent bonds, the typical materials are organic molecular crystals with intriguing properties such as semiconductor, [53] porosity, [68] etc. Owing to the inefficient packing of organic building blocks in the crystal state, some molecular crystals display extrinsic porosity, which are often termed as hydrogen-bonded organic frameworks (HOFs) [74,75] or supramolecular organic frameworks (SOFs). [76][77][78][79][80] For COMs connected by covalent bonds, typical materials are crystalline covalent organic frameworks (COFs), which were firstly reported in 2005 by Yaghi and co-workers [44] Benefitting from rigid chemical bonds and building blocks, COFs show permanent and well-ordered porosity. [45][46][47][48] Supramolecular-macrocycle-based COMs, a class of COMs with macrocycles as the main building blocks, have drawn particular attention in recent years. According to their components, supramolecular-macrocycle-based COMs can be classified into two main categories, the ones composed of pure macrocycles and the others consisting of macrocycles and other simple organic building blocks. Owing to their prefabricated cavities of a certain type, some of macrocycle-based COMs exhibit intrinsic microporosity for guest adsorption in the solid state. On the other hand, the extrinsic porosity of some macrocyclebased COMs may form due to the inefficient packing of these rigid macrocyclic molecules in the crystalline state. In certain circumstances, both intrinsic and extrinsic microporosity can be created in a single lattice of a certain COM, thus leading to Supramolecular macrocycles are well known as guest receptors in supramolecular chemistry, especially host−guest chemistry. In addition to their wide applications in host−guest chemistry and related areas, macrocycles have also been employed to construct crystalline organic materials (COMs) owing to their particular structur...

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Section: Other Supramolecular‐macrocycle‐based Comsmentioning

confidence: 99%

Section: Other Supramolecular‐macrocycle‐based Comsmentioning

confidence: 99%

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

et al. 2019

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“…19 This protected pyridyl bis-urea macrocycle lacks the urea N-H hydrogen bond donors that drive the self-assembly in other bis-urea macrocycles to afford columnar structures. Thus, it is more soluble in typical organic solvents and provides a building block for co-crystal formation that can act only as a halogen bond or hydrogen bond acceptor.…”

Section: Resultsmentioning

confidence: 99%

“…[15][16][17][18] In contrast, the pyridyl macrocycle 2 forms columnar assemblies through two separate hydrogen bonding interactions between the urea N-H's and two different acceptors: the urea carbonyl oxygen and the pyridine nitrogen. 19 The electrostatic potential distributions of these macrocycles highlight these basic sites (shown in red) that are primarily localized on the urea oxygens and the pyridine nitrogens. We set out to examine the propensity of pyridyl bis-ureas 1 and 2 to cocrystallize with halogen bond donors.…”

Section: Introductionmentioning

confidence: 99%

Short, strong halogen bonding in co-crystals of pyridyl bis-urea macrocycles and iodoperfluorocarbons

et al. 2013

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“…the urea O and pyridine N atom, forming N-HÁ Á ÁO and N-HÁ Á ÁN hydrogen bonds ( Fig. 1) (Roy et al, 2011). The assembly leaves the basic oxygen lone pairs on the exterior of the pillars of (1), which participate in noncovalent interactions with acidic alcohols for a wide range of pK a values ranging from 5.5 for tetrafluorophenol to 12.5 for trifluoroethanol (TFE), as well as acting as acceptors for halogen bonds with active donors, such as pentafluoroiodobenzene and diiodotetrafluorobenzenes (Roy et al, 2011(Roy et al, , 2012Som et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Temperature-induced pseudopolymorphism of molecular salts from a pyridyl bis-urea macrocycle and naphthalene-1,5-disulfonic acid

et al. 2018

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Molecular salts, often observed as cocrystals, play an important role in the fields of pharmaceutics and materials science, where salt formation is used to tune the properties of active pharmaceutical ingredients (APIs) and improve the stability of solid-state materials. Salt formation via a proton-transfer reaction typically alters hydrogen-bonding motifs and influences supramolecular assembly patterns. We report here the molecular salts formed by the pyridyl bis-urea macrocycle 3,5,13,15,21,22-hexaazatricyclo[15.3.1.1]docosa-1(21),7(22),8,10,17,19-hexaene-4,14-dione, (1), and naphthalene-1,5-disulfonic acid (HNDS) as two salt cocrystal solvates, namely 4,14-dioxo-3,5,13,15,21,22-hexaazatricyclo[15.3.1.1]docosa-1(21),7(22),8,10,17,19-hexaene-21,22-diium naphthalene-1,5-disulfonate dimethyl sulfoxide disolvate, CHNO·CHOS·2CHOS, (2), and the corresponding monosolvate, CHNO·CHOS·CHOS, (3). This follows the ΔpK rule such that there is a proton transfer from HNDS to (1), forming the reported molecular salts through hydrogen bonding. Prior to salt formation, (1) is relatively planar and assembles into columnar structures. The salt cocrystal solvates were obtained upon slow cooling of dimethyl sulfoxide-acetonitrile solutions of the molecular components from two temperatures (363 and 393 K). The proton transfer to (1) significantly alters the conformation of the macrocycle, changing the formerly planar macrocycle into a step-shaped conformation with trans-cis urea groups in (2) or into a bowl-shape conformation with trans-trans urea groups in (3).

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Guest induced transformations of assembled pyridyl bis-urea macrocycles

Abstract: Pyridine macrocycles with no cavities assembled into close packed columns yet absorbed guests including hydrogen, carbon dioxide, and iodine.

Cited by 31 publications

References 25 publications

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

Short, strong halogen bonding in co-crystals of pyridyl bis-urea macrocycles and iodoperfluorocarbons

Temperature-induced pseudopolymorphism of molecular salts from a pyridyl bis-urea macrocycle and naphthalene-1,5-disulfonic acid

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