Über Abkömmlinge des Pyrens

Lock, Gunther

doi:10.1002/cber.19370700510

Cited by 18 publications

(6 citation statements)

References 9 publications

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“…The second of these was prepared from b 2,6-dichlorobenzaldehyde (Frinton) by treatment with 13c-methyl of 6~ when 8 is 90". The mechanism of coupling therefore magn,sium iodide in ether (7), prepared from 13c enriched CH31…”

Section: ------X-----'50mentioning

confidence: 99%

The carbonyl group as a reluctant transmitter of hyperconjugative or σ–π spin–spin coupling interactions in derivatives of benzaldehyde, acetophenone, and benzophenone

Schaefer¹,

Peeling²,

Penner³

et al. 1986

Can. J. Chem.

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Unlike their counterparts in anisole or toluene derivatives, the six-bond spin-spin coupling constants between para ring protons or 19F nuclei and protons or 13c nuclei in the sidechain of derivatives of benzaldehyde, acetophenone, and benzophenone can apparently contain components of opposite sign, at least for the fluorine derivatives. The u-7i components are much smaller in magnitude than in toluene derivatives, leading to very small or unobservable coupling constants. Consequently they are of limited use in conformational analysis. INDO MO FPT computations and their modifications are examined as to the reasons for the small o-TI magnitudes. Although the spin polarizability of the 2pz orbital on oxygen appears to play an important role in the transmission of nuclear spin state information, the computations do not account for a "F coupling mechanism that appears to be significant for planar conformations. On the other hand, spin-spin coupling constants over five formal bonds to meta protons are sizeable and stereospecific.TED SCHAEFER, JAMES PEELING, GLENN H. PENNER et ALBERTA LEMIRE. Can. J. Chem. 64, 1859 (1986).Contrairement leurs contreparties dans les dCrivCs de l'anisole ou du toluene, les constantes de couplage spin-spin a travers six liaisons, entre les protons du cycle en position para ou les noyaux de I9F et les protons ou les noyaux de I3C de la chaine laterale des dCrivCs du benzaldehyde, de I'acCtophCnone et de la benzophCnone peuvent apparernment contenir des composants de signes opposes, au moins dans les derivCs fluores. Les constituants a-7i ont une intensit6 infkrieure a celle des dCriv6s du toluene conduisant ainsi a des constantes de couplage tr&s faibles qu'on ne peut observer. En consequence, ces constantes sont trbs peu utiles dans l'analyse conformationnelle. On a utiIisC des calculs INDO OM FPT ainsi que leurs modifications pour dCterminer les causes des faibles intensitks des constituants cr-TI. Bien que la polarisabilitk du spin de l'orbitale 2pz de I'oxygkne semble jouer un r6le important dans la transmission de I'information sur 1'Ctat du spin nuclkaire, les calculs ne tiennent pas compte du mCcanisme de couplage du 19F qui semble Ctre important dans les conformations planes. Par ailleurs, les constantes de couplage spin-spin a travers cinq liaisons formelles par rapport aux protons en position meta sont quantifiables et stCrCospCcifiques.[Traduit par la revue]

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Section: ------X-----'50mentioning

confidence: 99%

The carbonyl group as a reluctant transmitter of hyperconjugative or σ–π spin–spin coupling interactions in derivatives of benzaldehyde, acetophenone, and benzophenone

Schaefer¹,

Peeling²,

Penner³

et al. 1986

Can. J. Chem.

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“…1-Bromopyrene was synthesized from pyrene according to Lock [16] and converted to pyren-1-yllithium using n-BuLi. Reaction of pyrenyllithium reagent with (S)-γ -benzyloxymethyl-γ -butyrolactone (4) gave a lactole, which, without further purification, was reduced using boron trifluoride etherate and triethylsilane to (S)-1-benzyloxy-5-pyren-1-ylpentan-2-ol (5) in 35% overall yield (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Pyrene Intercalating Nucleic Acids With a Carbon Linker

Østergaard

Wamberg

Pedersen

2011

Nucleosides, Nucleotides and Nucleic Acids

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We have synthesized a carbon linker analogue of INA (oligonucleotides containing insertions of 1-O-(1-pyrenylmethyl)glycerol). Thermal stability studies showed an increase in melting temperature in favor of the carbon linker analogue. We also synthesized a carbon linker analogue with two pyrenes geminally attached. Fluorescence studies of this intercalating nucleic acid with the pyrene moieties inserted as a bulge showed formation of an excimer band. When a mismatch was introduced at the site of the intercalator, an excimer band was formed for the destabilized duplexes whereas an exciplex band was observed when the stability of the duplex was retained.

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“…Synthesis. The experimental procedures for some of the components of the multilayered systems were reported previously. , 1,6-Bis(2‘,6‘-dicarboxypyridyl-4‘-oxymethyl)pyrene was synthesized from pyrene and diethyl 4-hydroxypyridine-2,6-dicarboxylate in a five-step synthesis following literature procedures. − The synthesis of the latter compound is described in a previous publication …”

Section: Methodsmentioning

confidence: 99%

Photocurrent Generation in Noncovalently Assembled Multilayered Thin Films

et al. 2008

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Multilayered photocurrent generating thin films were fabricated by templated noncovalent assembly via stepwise assembly of molecular components. Each of films I-IV contained an underlying self-assembled monolayer (SAM) consisting of an alkanethiol linked covalently to a 2,6-dicarboxypyridine ligand that served as a binding site for attaching additional molecular components. The SAM subsequently was functionalized by sequential deposition of Cu(II), Co(II), or Fe(III) ions followed by a variety of substituted 2,6-dicarboxypyridine ligands as a means to incorporate one or more layers of pyrene chromophores into the film. The films were characterized by contact angle measurements, ellipsometry, grazing incidence IR, cyclic voltammetry, and impedance spectroscopy after deposition of each layer, confirming the formation of ordered, stable layers. Following incorporation into a three-electrode system, photoexcitation resulted in the generation of a cathodic photocurrent in the presence of methyl viologen and an anodic photocurrent in the presence of triethanolamine. Using this strategy, systems were fabricated that produced up to 89 nA/cm(2) of reproducible photocurrent.

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Über Abkömmlinge des Pyrens

Abstract: P i k r i u s~u r e -V e r b i n d u n g : 0.2 g 3-Cyan-pyren und 0.5 g P i k r i n s a u r e werden in 50 ccm kochendem dthanol geliist und eingeengt, bis beim Erkalten ziegelrote Krystalle vom Schmp. 141" (korr.) ausfallen. 60*

Cited by 18 publications

References 9 publications

The carbonyl group as a reluctant transmitter of hyperconjugative or σ–π spin–spin coupling interactions in derivatives of benzaldehyde, acetophenone, and benzophenone

The carbonyl group as a reluctant transmitter of hyperconjugative or σ–π spin–spin coupling interactions in derivatives of benzaldehyde, acetophenone, and benzophenone

Pyrene Intercalating Nucleic Acids With a Carbon Linker

Photocurrent Generation in Noncovalently Assembled Multilayered Thin Films

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