Supramolecular [2]pseudo-rotaxane polymer containing blue anthracene donor guest and green naphthalimide acceptor host as a FRET-ON sensor for hydrogen sulfide detection

Gouda, Chinmayananda; Pham, Be-Nhi; Nhien, Pham Quoc; Cuc, Tu Thi Kim; Weng, Chang Ching; Wu, Chia‐Hua; Wu, Judy I.; Li, Yaw-Kuen; Lin, Hong‐Cheu

doi:10.1016/j.dyepig.2022.110873

Cited by 5 publications

(5 citation statements)

References 55 publications

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“…The field of host-guest chemistry has very many important applications, including the purification of wastewater, the removal of toxins from ailing patients, chemosensing, the resolution of racemates, to modify chromatographic stationary phases for specific separations, for drug stability and transport and, also, the separation of positional isomers, to mention only a few [10][11][12][13][14][15][16]. The focus in our laboratories has been on the latter application type.…”

Section: Introductionmentioning

confidence: 99%

Exploring the host compound dynamics of 1,4-phenylene-bis(di-p-fluorophenylmethanol) in mixed pyridines

Barton,

Vorgers,

Hosten

2024

Preprint

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In this investigation, the wheel-and-axle host compound, 1,4-phenylene-bis(di-p-fluorophenylmethanol) H, was demonstrated to have inclusion ability for each of PYR, 2MP, 3MP and 4MP (1:1, 1:2, 1:2 and 1:2 were the H:G ratios). In the equimolar guest competition experiments, H was observed to have an overwhelming affinity for PYR and 4MP relative to 2MP and 3MP. In fact, selectivity coefficients calculated from the non-equimolar binary guest competition experiments suggested that this host compound would be an efficient candidate for the separation of all PYR/2MP mixtures and a 40:60 4MP/3MP solution through host-guest chemistry strategies. SCXRD analyses established the preferred guests (PYR and 4MP) to be involved in significantly shorter stabilizing classical hydrogen bonding interactions with H, explaining the selectivity behaviour of this host compound in the guest mixtures. Additionally, Hirshfeld surface considerations also explained this behaviour, but only for PYR. Additionally, thermal analyses were used to ascertain the relative thermal stabilities of the four complexes and, satisfyingly, the PYR- and 4MP-containing complexes possessed the greater thermal stabilities compared with H·2(2MP) and H·2(3MP), as was demonstrated by a comparison of their guest release onset temperatures.

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Section: Introductionmentioning

confidence: 99%

Exploring the host compound dynamics of 1,4-phenylene-bis(di-p-fluorophenylmethanol) in mixed pyridines

Barton,

Vorgers,

Hosten

2024

Preprint

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“…Furthermore, host compounds have further applications in chemosensing, removing hazardous substances from the environment and in chromatography [9][10][11]. In the pharmaceutical industry, cyclodextrins, more especially, have been found to be extremely useful for stabilizing active pharmaceutical ingredients and to assist in drug transport and delivery to the desired target site [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Crystallization experiments of the wheel-and-axle host compound, 1,4-phenylene-bis(di-p-tolylmethanol), from pyridine and methylpyridine mixtures

Barton,

Vorgers,

Hosten

2024

Preprint

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1,4Phenylene-bis(diptolylmethanol) (H), a host compound with the wheel-and-axle design, formed complexes with organic guest solvents pyridine (PYR) and 2-, 3- and 4-methylpyridine (2MP, 3MP and 4MP). The host:guest (H:G) ratios were 1:3, 1:2, 1:2 and 1:1, respectively. Host crystallization experiments from mixed guests demonstrated H to prefer both PYR and 4MP; however, it was established that these difficult-to-separate (by fractional distillations) guest mixtures cannot be purified/separated by means of H through supramolecular chemistry strategies owing to these selectivities for PYR and 4MP being less than optimal. Single crystal X-ray diffraction experiments showed that each guest compound was held in its complex by means of a classical hydrogen bond with H, and that one of the preferred guests, PYR, experienced a significantly shorter contact of this type than the other guests. Hirshfeld surface analyses demonstrated that PYR was also involved in a greater percentage of (guest)N···H(host) interactions compared with the other guest molecules. Thermal analyses, on the other hand, revealed that 4MP (also a favoured guest species) formed the most stable complex of the four in this investigation. These results with H were compared to those obtained when employing a closely related host compound from a previous report, 1,4-bis(diphenylhydroxymethyl)benzene: while both host species preferred the same guests (PYR and 4MP), the extent of the selectivity of that host compound compared with H in the present work was significantly more enhanced. Thus, minor modifications may deleteriously affect the selectivity behaviour of closely related host compounds.

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“…The applications of host–guest chemistry are vast and far-reaching. As an example, many biologically active compounds found in food, cosmetics, and pharmaceuticals suffer from low bioavailability and water insolubility, as well as having chemical instability, ensuring that their absorption into the human body is less than optimal, and cyclodextrins have been used extensively as host compounds to stabilize and improve the bioavailability of many of these compounds. − Other applications include removing toxins from the environment, chromatographic applications, isomer separations, and chemosensing. − …”

Section: Introductionmentioning

confidence: 99%

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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Supramolecular [2]pseudo-rotaxane polymer containing blue anthracene donor guest and green naphthalimide acceptor host as a FRET-ON sensor for hydrogen sulfide detection

Cited by 5 publications

References 55 publications

Exploring the host compound dynamics of 1,4-phenylene-bis(di-p-fluorophenylmethanol) in mixed pyridines

Exploring the host compound dynamics of 1,4-phenylene-bis(di-p-fluorophenylmethanol) in mixed pyridines

Crystallization experiments of the wheel-and-axle host compound, 1,4-phenylene-bis(di-p-tolylmethanol), from pyridine and methylpyridine mixtures

Crystal Growth of Host Compound DED and Derivatives in Alkylbenzenes

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