Cup-shaped<i>E</i>,<i>E</i>-stilbenophane: synthesis, crystal structure and supramolecular chemistry

Darabi, Hossein Reza; Farahani, Abbas Darestani; Karouei, Mohammad Hashemi; Aghapoor, Kioumars; Firouzi, Rohoullah; Herges, Rainer; Mohebbi, Ali; Näther, Christian

doi:10.1080/10610278.2012.678359

Cited by 16 publications

(5 citation statements)

References 22 publications

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“…According to our synthetic strategy, a twofold intramolecular McMurry reaction was considered first (Scheme 5). Due to lack of in depth experience, the used reaction conditions were inspired by protocols applied to aryl‐aldehydes [46] and enabled intramolecular cyclizations [47] . Thus the tetra aldehyde 14 dissolved in THF was added to a 0 °C cold solution of titanium tetrachloride (TiCl 4 , 4 equiv) and zinc dust (Zn, 12 equiv) under an argon protection gas atmosphere.…”

Section: Resultsmentioning

confidence: 99%

“…Due to lack of in depth experience, the used reaction conditions were inspired by protocols applied to aryl‐aldehydes [46] and enabled intramolecular cyclizations. [47] Thus the tetra aldehyde 14 dissolved in THF was added to a 0 °C cold solution of titanium tetrachloride (TiCl 4 , 4 equiv) and zinc dust (Zn, 12 equiv) under an argon protection gas atmosphere. After refluxing the reaction mixture for about 16 h and work up, the desired doubly cyclized target structure 1 was isolated in 8.5 % yield by CC.…”

Section: Resultsmentioning

confidence: 99%

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An Ortho‐Tetraphenylene‐Based “Geländer” Architecture Consisting Exclusively of 52 sp²‐Hybridized C Atoms

Dekkiche

Malinčík

Prescimone

et al. 2021

Chemistry A European J

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A new type of "Geländer" molecule based on a ortho-tetraphenylene core is presented. The central paraquaterphenyl backbone is wrapped by a 4,4'-di((Z)-styryl)-1,1'biphenyl banister, with its aryl rings covalently attached to all four phenyl rings of the backbone. The resulting helical chiral bicyclic architecture consists exclusively of sp 2 -hybridized carbon atoms. The target structure was assembled by expanding the central ortho-tetraphenylene subunit with the required additional phenyl rings followed by a twofold macrocyclization. The first macrocyclization attempts based on a twofold McMurry coupling were successful but low yielding; the second strategy, profiting from olefin metathesis, provided satisfying yields. Hydrogenation of the olefins resulted in a saturated derivative of similar topology, thereby allowing the interdependence between saturation and physico-chemical properties to be studied. The target structures, including their solid-state structures, were fully characterized. The helical chiral bicycle was synthesized as a racemate and separated into pure enantiomers by HPLC on a chiral stationary phase. Comparison of recorded and simulated chiroptical properties allowed the enantiomers to be assigned.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

An Ortho‐Tetraphenylene‐Based “Geländer” Architecture Consisting Exclusively of 52 sp²‐Hybridized C Atoms

Dekkiche

Malinčík

Prescimone

et al. 2021

Chemistry A European J

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“…In continuation of our ongoing research in the design and synthesis of various chemosensors [52][53][54][55][56][57][58][59][60][61][62][63][64],…”

Section: Introductionmentioning

confidence: 98%

Fast, Selective and Sensitive Fluorescence Detection of Levofloxacin, Fe3+ and Cu2+ Ions in 100% Aqueous Solution Via Their Reciprocal Recognition

Nazarian,

Darabi,

Aghapoor

et al. 2023

J Fluoresc

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The fluorescence detection of ions and pharmaceutical effluents by using organic chemosensors is a valuable surrogate to the currently existing expensive analytical methods. In this regard, the design of multi-functional chemosensors to recognize desirable guests is of utmost importance. In this study, we first show that levofloxacin (LVO) is able to use as a fluorescent chemosensor for the detection of biologically important Cu 2+ (turn-off) and Fe 3+ (turn-on) ions via independent signal outputs in 100% aqueous buffer solutions. Next, using the reciprocal recognition of LVO and Fe 3+ provides a unique emission pattern for the detection of LVO. This approach exhibited a high specificity to LVO among various pharmaceutical samples, namely acetaminophen (AC), azithromycin (AZ), gemifloxacin (GEM) and ciprofloxacin (CIP) and also showed great antiinterference property in urine. The attractive features of this sensing system are availability, easy-to-use, high sensitivity (limit of detection = 18 nM for Cu 2+ , 22 nM for Fe 3+ and 0.12 nM for LVO), rapid response (5 s) with an excellent selectivity.

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“…In light of the signi cance of uorescent cyclophanes in the detection of guest molecules [21], and in line with our ongoing research in supramolecular chemistry and chemical sensing [22][23][24][25][26][27][28][29][30][31][32][33][34][35], we are excited to present the introduction of new acetalophanes 1a-c. These compounds have the potential to serve as "ON-OFF" uorescent sensors for the detection of Fe 3+ ions through deacetalization.…”

Section: Introductionmentioning

confidence: 99%

Rapid, Sensitive, and Selective "ON–OFF" Detection of Fe3+ Ions Using Novel Acetalophanes and Their Applications in Real Samples

Sobhani,

Darabi,

Atasbili

et al. 2024

J Fluoresc

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Three novel acetalophanes 1a-c have been designed, synthesized and characterized. The receptors 1b-c, featuring bulky anthracene groups, displayed signi cant selectivity for Fe 3+ ions, resulting in a turn-off uorescence mode in a DMF-buffer solution. Conversely, the non-steric probe 1a could serve as a versatile sensor for the simultaneous detection of Fe 3+ and Cu 2+ ions in MeOH-buffer solution. The sensing mechanism for the capability of 1a was demonstrated to be different, as evidenced by the addition of cyanide ions. The probes with Fe 3+ exhibited a sensing mechanism that resulted in the deprotection of acetals to the corresponding starting materials, as con rmed by 1 H NMR, IR spectra and TLC analysis. The attractive features of these practical and e cient sensors are selectivity, sensitivity (limit of detection = 0.15 µM by 1a, 0.16 µM by 1b and 0.14 µM by 1c), rapid response (less than 5 seconds). The on-site monitoring of various real samples, including well water, apricot, and green tea, proved to be successful for the quantitative and cost-effective detection of Fe 3+ . The method demonstrated good precision, even in the presence of other interfering materials.

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Cup-shapedE,E-stilbenophane: synthesis, crystal structure and supramolecular chemistry

Cited by 16 publications

References 22 publications

An Ortho‐Tetraphenylene‐Based “Geländer” Architecture Consisting Exclusively of 52 sp²‐Hybridized C Atoms

An Ortho‐Tetraphenylene‐Based “Geländer” Architecture Consisting Exclusively of 52 sp²‐Hybridized C Atoms

Fast, Selective and Sensitive Fluorescence Detection of Levofloxacin, Fe3+ and Cu2+ Ions in 100% Aqueous Solution Via Their Reciprocal Recognition

Rapid, Sensitive, and Selective "ON–OFF" Detection of Fe3+ Ions Using Novel Acetalophanes and Their Applications in Real Samples

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Cup-shapedE,E-stilbenophane: synthesis, crystal structure and supramolecular chemistry

Cited by 16 publications

References 22 publications

An Ortho‐Tetraphenylene‐Based “Geländer” Architecture Consisting Exclusively of 52 sp2‐Hybridized C Atoms

An Ortho‐Tetraphenylene‐Based “Geländer” Architecture Consisting Exclusively of 52 sp2‐Hybridized C Atoms

Fast, Selective and Sensitive Fluorescence Detection of Levofloxacin, Fe3+ and Cu2+ Ions in 100% Aqueous Solution Via Their Reciprocal Recognition

Rapid, Sensitive, and Selective "ON–OFF" Detection of Fe3+ Ions Using Novel Acetalophanes and Their Applications in Real Samples

Contact Info

Product

Resources

About

An Ortho‐Tetraphenylene‐Based “Geländer” Architecture Consisting Exclusively of 52 sp²‐Hybridized C Atoms

An Ortho‐Tetraphenylene‐Based “Geländer” Architecture Consisting Exclusively of 52 sp²‐Hybridized C Atoms