Template directed photodimerization of trans-1,2-bis(n-pyridyl)ethylenes and stilbazoles in water

Pattabiraman, Mahesh; Natarajan, Arunkumar; Kaliappan, Raja; Mague, Joel T.; Ramamurthy, V.

doi:10.1039/b508458j

Cited by 155 publications

(98 citation statements)

References 32 publications

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“…Weil Cucurbit [8]uril zwei Moleküle aufzunehmen vermag, wurde es als Nano-Reaktionsgefäß [170] oder als Komponente von molekularen Maschinen in Wasser genutzt. [154,156] Kürz-lich wurde eine redoxgetriebene molekulare Maschine -ein "molekulares Kettenschloss" -beschrieben, die auf diesem Phänomen beruht.…”

Section: Methodsunclassified

Supramolekulare Chemie in Wasser

2007

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Die supramolekulare Chemie in Wasser ist ein ständig wachsendes Forschungsgebiet, da nichtkovalente Wechselwirkungen in wässrigen Medien entscheidend für ein besseres Verständnis und die Kontrolle grundlegender Prozesse in der Natur sind. Dieser Aufsatz bietet einen Überblick über aktuelle Entwicklungen auf den Gebieten der wasserlöslichen synthetischen Rezeptoren, der Selbstorganisation und der molekularen Erkennung in Wasser unter Berücksichtigung von Funktionalitäten, die zur Verbesserung der Wasserlöslichkeit eingeführt werden, sowie der supramolekularen Wechselwirkungen und der Methoden, die für eine effiziente Gasterkennung und Selbstorganisation in Wasser eingesetzt werden. Zudem beschreibt er die besonderen Eigenschaften und Anwendungsmöglichkeiten supramolekularer Einheiten in wässrigen Medien.

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Section: Methodsunclassified

Supramolekulare Chemie in Wasser

2007

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“…26 Protonated stilbazoles (styrylpyridinium salts) also form inclusion compounds in CB [8], which behave similarly to the aforementioned unsymmetrical 1,2 -dipy ridiniumethylenes. 19,27 Anachenko et al 28 and Kaliappan et al 29 investigated the effect of calixarene hosts on the photochemistry of stilbenes and stilbazoles, respectively. Their fi ndings are in agreement with the intervention of the calixarene host as moderately effi cient template for the formation of photodimers, consistent with the more fl exible nature of CAs compared with CDs and CBs.…”

Section: Templated (2 π + 2 π ) Photocyclization Reactions In Solutionmentioning

confidence: 99%

Templating Photoreactions in Solution

Bassani

2011

Supramolecular Photochemistry

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“…The stereoselectivity of photodimerization in the presence of CB [8] ( syn / anti = 95/5) is much better than that obtained with γ -CD ( syn / anti = 80/20 Irradiation of trans -1,2 -bis(4 -pyridyl)ethylene dihydrochloride in the presence of CB [8] also yields the syn -dimer as major product in 90% relative yield and anti -dimer in only 4% relative yield. 56 However, in the presence of CB [7], no [2+2] dimerization product was obtained and only cis -1,2 -bis(4 -pyridyl)ethylene was formed. This result is attributed to the different complexation stoichiometry of 1,2 -bis(4 -pyridyl)ethylene with CB [7] (1 : 1) and CB [8] (2 : 1).…”

Section: Supramolecular Photoreactions With Cucurbiturilsmentioning

confidence: 99%

Reaction Control by Molecular Recognition – A Survey from the Photochemical Perspective

Yang

Liu

et al. 2010

Molecular Encapsulation

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Molecular recognition through non -covalent interactions between two or more molecules has attracted much attention from a broad spectrum of chemists for a long period of time and has already found many applications in various areas of science and technology. The concept of molecular recognition was fi rst developed for biomolecular systems such as enzyme, antibody and DNA, which can selectively bind the specifi c target molecules through non -covalent weak interactions, including hydrogen bonding, van der Waals, dipole -dipole, charge -dipole and hydrophobic interactions. 1 -3 Recent studies on artifi cial host -guest systems have revealed that molecular recognition is the essential conceptual basis for supramolecular chemistry and nanotechnology. 4,5 Reaction control through complexation of substrate by supramolecular host is a relatively new idea compared to the conventional approaches that involve simple collisional attack or coordination of substrate to metal. Multiple non -covalent interactions in supramolecular assembly bind and locate a site -specifi c substrate in the right position, orientation and conformation near the catalyst or active site, stabilize the high -energy transition state, and eventually make the reaction faster and more selective. Typical examples are found in enzymatic reactions, which proceed with high specifi city and effi ciency in aqueous solutions under mild conditions. These observations in natural systems have inspired Molecular Encapsulation: Organic Reactions in Constrained SystemsEdited by Udo H. Brinker and Jean-Luc Mieusset

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Template directed photodimerization of trans-1,2-bis(n-pyridyl)ethylenes and stilbazoles in water

Abstract: Template induced photodimerization of trans-1,2-bis(n-pyridyl)ethylene dihydrochlorides and trans-n-stilbazole hydrochlorides within cucurbit[8]uril in aqueous media leads to high yields of the syn dimer.

Cited by 155 publications

References 32 publications

Supramolekulare Chemie in Wasser

Supramolekulare Chemie in Wasser

Templating Photoreactions in Solution

Reaction Control by Molecular Recognition – A Survey from the Photochemical Perspective

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