Complementary host behaviour of three anthracenyl-derived roof-shaped compounds in mixed pyridines

Barton, Benita; Caira, Mino R.; Senekal, Ulrich; Hosten, Eric C.

doi:10.1039/d3ce00080j

Cited by 7 publications

(10 citation statements)

References 51 publications

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“…As reported before for the 3(H3)•o-Xy complex, 50 Furthermore, as in H4•2MP and H4•4MP, 49 two TOL guests were retained in the complex by means of six H4 molecules, forming discrete cavities around them, as described by an earlier figure (Figure 3d). Interestingly, no host•••guest interactions were present in the H4 and TOL complex (and no host•••guest interactions could be observed in H4•EB due to the excessive guest disorder and SQUEEZE procedure implementation).…”

Section: Host Crystallization Experiments From Mixed Guests Tablesupporting

confidence: 73%

“…Furthermore, as in H4 ·2MP and H4 ·4MP, two TOL guests were retained in the complex by means of six H4 molecules, forming discrete cavities around them, as described by an earlier figure (Figure d).…”

Section: Resultsmentioning

confidence: 65%

“…In 3( H3 )·EB, EB was disordered around a 2-fold rotation axis and an inversion point. Interestingly, the crystal structure of H4 ·TOL was found to be isostructural with H4 ·2-MP and H4 ·4-MP (where MP is methylpyridine), the crystal structures of which were reported earlier, while the unit cell parameters of 2( H3 )·TOL and 3( H3 )·EB resemble those of 3( H3 )· o -Xy ( ortho -xylene) . The EB guest molecules in H4 ·EB experienced excessive disorder which could not be modeled and so required implementation of the SQUEEZE procedure during structure refinement.…”

Section: Resultsmentioning

confidence: 80%

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Crystal Growth of Host Compound DED and Derivatives in Alkylbenzenes

Barton,

Caira,

Senekal

et al. 2024

Crystal Growth & Design

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Crystal growth of host compound trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (H1, DED) and three derivatives thereof (H2–H4) from potential guest solvents toluene (TOL), ethylbenzene (EB), and cumene (CUM) revealed that each one has the ability to enclathrate one, some, or all of these guest species. In equimolar TOL/CUM mixtures, H4 displayed an increased affinity for TOL (86.1%) compared with H2 (62.4%), while these selectivities for this guest species were only moderate when crystallization was from the equimolar mixed ternary guests (56.9 and 51.1%, respectively). H1 and H3, on the other hand, formed a mixed complex only in the equimolar TOL/EB solution, the remaining experiments furnishing a guest-free apohost compound only. Importantly, since various procedures in the industry yield mixtures of these alkylbenzenes, H4 was shown to be a likely candidate for the separation of both TOL from the TOL/CUM and EB from EB/CUM mixtures (the averaged selectivity coefficients, K, were high, 13.7 and 12.1, respectively). SCXRD experiments showed that EB in 3H3·EB experienced a significantly shorter (host)C–H···π(guest) interaction (2.50 Å) than TOL in its complex with H3 (2.87, 2.66 Å), in accordance with the higher affinity of H3 for EB relative to that for TOL. The H4·TOL and H4·EB complexes experienced analogous host···host interactions, but host···guest contacts could not be compared since the SQUEEZE function in PLATON was required during the refinement of the crystal structure of H4·EB to deal with severe guest disorder. Thermal analyses showed that the preferred guest of H3 (EB) formed a complex with a greater relative thermal stability compared with less favored TOL. Finally, this investigation has shown that the size of the alkyl group bonded to the aromatic ring of the guest species affects the selectivity behavior of each host compound. CUM, which has the largest alkyl substituent of the three guest species, was not ever preferred by any of the four host compounds investigated here.

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Section: Host Crystallization Experiments From Mixed Guests Tablesupporting

confidence: 73%

Section: Resultsmentioning

confidence: 65%

Section: Resultsmentioning

confidence: 80%

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Crystal Growth of Host Compound DED and Derivatives in Alkylbenzenes

Barton,

Caira,

Senekal

et al. 2024

Crystal Growth & Design

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“…In our own laboratories, investigations into the employment of host–guest chemistry for the challenging separations of difficult-to-separate mixtures are ongoing. More specifically, the synthesis and selectivity behaviour of host compounds derived from tartaric acid, 17 xanthone and thioxanthone, 18 and anthracene 19 have been analysed in mixtures of isomers with commendable outcomes. To illustrate, the host compound DED ( trans -9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid) was assessed for its potential to separate the DCBs with remarkable results: this roof-shaped compound was observed to have a complete selectivity towards p -DCB when crystallized from various mixtures of the DCBs.…”

Section: Introductionmentioning

confidence: 99%

Host compounds based on the rigid 9,10-dihydro-9,10-ethanoanthracene framework: selectivity behaviour in mixed isomeric dichlorobenzenes

Barton,

Caira,

Senekal

et al. 2024

CrystEngComm

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The behaviour of host compounds dimethyl trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate (H1), trans-α,α,α′,α′-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (H2) and trans-α,α,α′,α′-tetra(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (H3), based on the rigid 9,10-dihydro-9,10-ethanoanthracene framework, was investigated in the presence of singular dichlorobenzene (o-DCB, m-DCB and...

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“…Our research group has considered host compounds based on tartaric acid, , fused tricyclic systems (xanthenyl and thioxanthenyl), − and roof-shaped anthracenyl-based molecules , for their selectivity behavior in these mixed pyridines with varying degrees of success. In most cases, the host selectivity behavior was dependent on the particular host compound employed.…”

Section: Introductionmentioning

confidence: 99%

Behavior of the Wheel-and-Axle Host Compound 1,4-Bis(diphenylhydroxymethyl)benzene in Mixed Pyridyl Guest Solvents

Barton,

Vorgers,

Hosten

2023

Crystal Growth & Design

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The host ability of the wheel-and-axle compound, 1,4-bis-(diphenylhydroxymethyl)benzene H, was extensively investigated in pure pyridine (PYR), 2-methylpyridine (2MP), 3-methylpyridine (3MP), and 4methylpyridine (4MP) guest pyridines; each one was enclathrated with 1:2 H/G ratios. H was then presented with mixed guest solvents, both equimolar and binary non-equimolar solutions, and it was observed that this host compound possesses the ability to separate or purify a great number of these various mixtures. The selectivity of H was demonstrated to be significantly in favor of PYR and 4MP dependent on the type and amount of each guest present in the solution. The crystal structures of the four single-solvent complexes were obtained by employing SCXRD analyses, which also assisted in understanding the host selectivity behavior in these mixed solvents. Hirshfeld surface investigations demonstrated that the preferred guest species, PYR and 4MP, experienced a greater percentage of (guest)N•••H−O(host) interactions than was observed for the guests less preferred (2MP and 3MP). Finally, data from thermal analyses concurred with some, but not all, of the observations made from the mixed guest solvent competition experiments.

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Complementary host behaviour of three anthracenyl-derived roof-shaped compounds in mixed pyridines

Cited by 7 publications

References 51 publications

Crystal Growth of Host Compound DED and Derivatives in Alkylbenzenes

Crystal Growth of Host Compound DED and Derivatives in Alkylbenzenes

Host compounds based on the rigid 9,10-dihydro-9,10-ethanoanthracene framework: selectivity behaviour in mixed isomeric dichlorobenzenes

Behavior of the Wheel-and-Axle Host Compound 1,4-Bis(diphenylhydroxymethyl)benzene in Mixed Pyridyl Guest Solvents

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