Encapsulation of Trimethine Cyanine in Cucurbit[8]uril: Solution versus Solid‐State Inclusion Behavior

Soavi, Giuseppe; Pedrini, Alessandro; Das, Anjali Devi; Terenziani, Francesca; Pinalli, Roberta; Hickey, Neal; Medagli, Barbara; Geremia, Silvano; Dalcanale, Enrico

doi:10.1002/chem.202200185

“…For the cationic trimethine cyanine within the cucurbit[8]uril (Figure 2A), [35] the interaction energies of the aISS structures are almost identical to those from the NCI‐iMTD algorithm. This indicates a similar structure quality and holds also for the electronically difficult cationic, open‐shell octamethylated‐naphthalene complex between naphthalene and anionic antimony hexafluoride (Figure 2D) [37] and the paramagnetic copper complex (Figure 2E) [38] .…”

Section: Resultsmentioning

confidence: 80%

“…To demonstrate the general applicability and efficiency of the aISS algorithm and to validate the resulting structures, we investigated a variety of currently researched dimers and trimers (Figure 2). [35–40] …”

Section: Resultsmentioning

confidence: 99%

“…To demonstrate the general applicability and efficiency of the aISS algorithm and to validate the resulting structures, we investigated a variety of currently researched dimers and trimers (Figure 2). [35][36][37][38][39][40] These small to medium-sized systems contain up to 300 atoms including heavy main-group elements and transition metals, which are usually challenging or not even included for common force fields that do not employ electronic information. Thus, the default GFN2-xTB [41] was chosen for the final geometry optimizations in the aISS algorithm (aISS//GFN2-xTB).…”

Section: General Applicability and Evaluationmentioning

confidence: 99%

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Automated and Efficient Generation of General Molecular Aggregate Structures

Plett

¹

2022

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Modeling intermolecular interactions of complex non-covalent structures is important in many areas of chemistry. To facilitate the generation of reasonable dimer, oligomer, and general aggregate geometries, we introduce an automated computational interaction site screening (aISS) workflow. This easy-to-use tool combines a genetic algorithm employing the intermolecular force-field xTB-IFF for initial search steps with the general force-field GFN-FF and the semi-empirical GFN2-xTB method for geometry optimizations. Compared with the alternative CREST program, aISS yields similar results but with computer time savings of 1-3 orders of magnitude. This allows for the treatment of systems with thousands of atoms composed of elements up to radon, e.g., metal-organic complexes, or even polyhedra and zeolite cut-outs which were not accessible before. Moreover, aISS can identify reactive sites and provides options like site-directed (user-guided) screening.

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“…For the single-structure aISS runtype, only the best GFN2-xTB structure was re-optimized. The resulting interaction energies are shown in Table 1 as absolute values and as percentages of E int relative to the For the cationic trimethine cyanine within the cucurbit- [8]uril (Figure 2A), [35] the interaction energies of the aISS structures are almost identical to those from the NCI-iMTD algorithm. This indicates a similar structure quality and holds also for the electronically difficult cationic, open-shell octamethylated-naphthalene complex between naphthalene and anionic antimony hexafluoride (Figure 2D) [37] and the paramagnetic copper complex (Figure 2E).…”

Section: General Applicability and Evaluationmentioning

confidence: 89%

Automated and Efficient Generation of General Molecular Aggregate Structures

Plett

¹

2022

View full text Add to dashboard Cite

Modeling intermolecular interactions of complex non-covalent structures is important in many areas of chemistry. To facilitate the generation of reasonable dimer, oligomer, and general aggregate geometries, we introduce an automated computational interaction site screening (aISS) workflow. This easy-to-use tool combines a genetic algorithm employing the intermolecular force-field xTB-IFF for initial search steps with the general force-field GFN-FF and the semi-empirical GFN2-xTB method for geometry optimizations. Compared with the alternative CREST program, aISS yields similar results but with computer time savings of 1-3 orders of magnitude. This allows for the treatment of systems with thousands of atoms composed of elements up to radon, e.g., metal-organic complexes, or even polyhedra and zeolite cut-outs which were not accessible before. Moreover, aISS can identify reactive sites and provides options like site-directed (user-guided) screening.

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“…Their uncommon binding nature make them superior host molecules and they play an important part in the design and constructions of novel host-guest (HÀ G) SPM compounds for the progress of molecular device. [11][12][13][14][15][16] Contrary to a covalent bond, the noncovalent interactions among the host and the guest are often reversible and stimuli-responsive, forming the basis of the design of dynamic HÀ G complexes with tunable properties. In 1905, the parent CB [6] was synthesized by Behrend and coworkers by condensation between glycoluril and formaldehyde under acidic conditions.…”

Section: Introductionmentioning

confidence: 99%

Emissive‐Dye/Cucurbit[n]uril‐Based Fluorescence Probes for Sensing Applications

Chatterjee

¹

,

Liang

²

2023

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Supramolecular host-guest chemistry has provided many opportunities for the design and construction of new fluorescent systems in various applications, particularly in the field of sensing. Owing to the special structure and fascinating utilities, cucurbit[n]urils (CB[n]s) existing themselves as a young family of molecular vessels, it construction a stable host-guest supramolecular complex with a variety of fluorescent dyes and indicators, that has been used as a powerful fluorescent probe and is widely used in sensing and related research fields. Therefore, in this review article, we will outline and attention on the recent advances in the progress of various CB[n] ⋅ guestbased fluorescent probes, it can provide a general overview of the construction, detection mechanism and fluorescence sensing of certain metal ions, biomolecules and toxic chemicals. Examples of the selection of other types of CB[n]-based supramolecular assemblies and coordination polymers will also be covered. Finally, we will also provide important views on fluorescent CB[n] ⋅ guest-based inclusion complex for metal ion and biomolecular sensors.

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Encapsulation of Trimethine Cyanine in Cucurbit[8]uril: Solution versus Solid‐State Inclusion Behavior

Abstract: Dedicated to Vincenzo Balzani on the occasion of his 85 th birthday.

Cited by 4 publications

References 47 publications

Automated and Efficient Generation of General Molecular Aggregate Structures

Automated and Efficient Generation of General Molecular Aggregate Structures

Automated and Efficient Generation of General Molecular Aggregate Structures

Emissive‐Dye/Cucurbit[n]uril‐Based Fluorescence Probes for Sensing Applications

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