The synthesis of a porphyrin with a hydrocarbon encapsulated face

Schnatter, Wayne F. K.; Almarsson, Ӧrn; Bruice, Thomas C.

doi:10.1016/s0040-4020(01)96191-5

Cited by 15 publications

(18 citation statements)

References 11 publications

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“…1 Methyl 3-(2-Vinylphenyl)propanoate (16): nBuLi (1.6  solution in hexane, 87.50 mL) was added at Ϫ20°C under argon to a suspension of methyltriphenylphosphonium bromide (50.300 g, 0.14 mol) in THF (150 mL). After the mixture had been kept at this temperature for 30 min, methyl 3-(2-formylphenyl)propanoate [20] (15, 21.100 g, 0.11 mol) was added over 15 min. The mixture was allowed to warm to room temp., and after one night the solvents were removed.…”

Section: Methodsmentioning

confidence: 99%

“…The styryl alcohol 2 was prepared in four steps, starting from the ester 15. [20] Methylenation of the aldehyde function, followed by reduction of the ester function, gave the alcohol 17, which was oxidized to the aldehyde 18. This was homologated to the aldehyde 20 in two steps, and reduction of the aldehyde function furnished the desired alcohol 2 (Scheme 2).…”

Section: Preparation Of Alcohols 1؊12mentioning

confidence: 99%

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Preparation of Oxocanes by Electrophilic Cyclizations of Unsaturated Alcohols in the Presence of Bis(collidine)halonium(I) Hexafluorophosphates

et al. 2003

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Keywords: Alcohols / Cyclic ethers / Cyclizations / Entropy / Medium-sized rings / Synthetic methods 7-Octen-1-ols substituted in the sp 3 −sp 3 carbon chain with carbocyclic (phenyl and cyclopropane) and heterocyclic (epoxide and dioxolane) moieties were prepared and their cyclizations in the presence of bis(collidine)iodonium(I) and -bromonium(I) hexafluorophosphates as electrophiles were studied. Oxocanes were obtained in modest to good yields when a rigid cyclic moiety (cyclopropane or phenyl) was present in the chain, while yields of cyclizations were lower if

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Section: Methodsmentioning

confidence: 99%

Section: Preparation Of Alcohols 1؊12mentioning

confidence: 99%

Preparation of Oxocanes by Electrophilic Cyclizations of Unsaturated Alcohols in the Presence of Bis(collidine)halonium(I) Hexafluorophosphates

et al. 2003

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“…Convergent synthesis of tetrakis(oligophenylene)benzene derivatives are executed by Suzuki cross coupling of the arms to a tetrabromo center 58a [154]. Tetrakis(oligo(phenylene ethenylene))benzene and tetrakis(oligo(ethenylene))benzene stars are obtained by Wittig [162,163] or Wittig-Horner reactions [164,165] with cores 61 , 62a , 62b or by Siegrist reaction [70] using durene 6 . Tetrakis(oligo(phenylene ethynylene))benzene and tetrakis(oligoethynylene)benzene molecules were prepared by the Hagihara-Sonogashira reaction from core reagents 58a , b [152,166].…”

Section: Star Compounds With a Benzene Corementioning

confidence: 99%

Star-Shaped Conjugated Systems

2010

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The present review deals with the preparation and the properties of star-shaped conjugated compounds. Three, four or six conjugated arms are attached to cross-conjugated cores, which consist of single atoms (B, C+, N), benzene or azine rings or polycyclic ring systems, as for example triphenylene or tristriazolotriazine. Many of these shape-persistent [n]star compounds tend to π-stacking and self-organization, and exhibit interesting properties in materials science: Linear and non-linear optics, electrical conductivity, electroluminescence, formation of liquid crystalline phases, etc.

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“…[10] The elongation unit 2 carriesa ni mine based Wittig-Horner reagent [11] to construct the first strand and am asked aldehyde( protected as diethyla cetal) as the buildingb lock of the second strand. Due to their efficiency in olefin synthesis, the Wittig-Horner reaction and aK noevenagel condensation were chosen to constructt he two strandso fp olyenei n the two stages.…”

Section: Resultsmentioning

confidence: 99%

Template‐Assisted Benzannulation Route to Pentacene and Tetracene Derivatives and its Application to Construct Amphiphilic Acenes That Self‐Assemble into Helical Wires

Pal

Chang

Zeng

et al. 2017

Chemistry A European J

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Pentacene is one of the most versatile organic semiconductors. New synthetic strategies to construct the pentacene skeleton are imperative to produce pentacene derivatives with appropriate solubility, stability, and optoelectronic properties for various applications. This paper describes a template-directed approach to pentacene derivatives. In the retrosynthesis, the acene skeleton is viewed as a laddered double strand polyene instead of the more intuitive linearly fused hexagons. Based on this vision, the template strand of polyene is constructed with Wittig olefination, whereas the second strand is accomplished with Knoevenagel condensation to produce pentacene and tetracene derivatives. The synthetic scheme is flexible enough to generate an array of acene derivatives with substitution patterns that were hitherto difficult to access. Amphiphilic pentacene and tetracene derivatives were also synthesized by the template strategy. One pentacene based amphiphilic rod-coil molecule undergoes self-assembly to form helical wire structures that were visualized with TEM.

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The synthesis of a porphyrin with a hydrocarbon encapsulated face

Cited by 15 publications

References 11 publications

Preparation of Oxocanes by Electrophilic Cyclizations of Unsaturated Alcohols in the Presence of Bis(collidine)halonium(I) Hexafluorophosphates

Preparation of Oxocanes by Electrophilic Cyclizations of Unsaturated Alcohols in the Presence of Bis(collidine)halonium(I) Hexafluorophosphates

Star-Shaped Conjugated Systems

Template‐Assisted Benzannulation Route to Pentacene and Tetracene Derivatives and its Application to Construct Amphiphilic Acenes That Self‐Assemble into Helical Wires

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