Herstellung konjugierter Polyene mit Anthryl- und<i>N</i>-Methylpyridinium- Endgruppen

Effenberger, Franz; Niesert, Claus-Peter

doi:10.1055/s-1992-26322

Cited by 13 publications

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“…Anthracene-polyene pyridinium compounds have been investigated first with respect to such kind of ordering of single molecules. 11,12 As amphiphiles these compounds are able to form ordered monolayers on the water/air surface which are transferable onto solid supports (e.g. glass) by the Langmuir-Blodgett technique.…”

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“…16 Dialdehydes are well known as starting materials in the synthesis of polyenals. 11 While crocetin dialdehyde (3a) has already been used successfully, 2,15-dimethyl-6,11diethylheptaenedial 3b was prepared for the first time as outlined in Scheme 1.…”

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“…Prior to use, the starting dialdehyde 1b 11,17 was purified by filtration on silica gel and subsequently irradiated at 360 nm for 16-18 h in the presence of catalytic amounts of I 2 to isomerize the cis-isomer to the all-trans compound 1b. Recrystallization from MeOH finally gave isomerically pure (all-E)-1b.…”

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“…Recrystallization from MeOH finally gave isomerically pure (all-E)-1b. In a twofold Wittig olefination analogous to a known method 18 1b was reacted with the phosphonium chloride 2 11,18 to give the hexadecaheptaenedial 3b.…”

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“…The preparation of the aryl-terminated polyenaldehydes 5, 6 by reaction of dialdehydes 1 and 3 with phosphonium bromides 4a, 11 and 4b-d, based on literature procedures, is shown in Scheme 2.…”

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Synthesis of Aryl-Terminated Polyenaldehydes and Polyenetriethoxysilanes for Preparation of Self-Assembled Monolayers on Silicon Surfaces

Effenberger¹,

Wezstein²

2001

Synthesis

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The synthesis of a,w-terminally functionalized polyenes with arenes or hetarenes at one end and either an aldehyde or a triethoxysilyl function at the other end, capable of reacting with H-terminated or oxidized silicon surfaces, is described. Analogous to known Wittig reactions, polyenedialdehydes 1 and 3, the latter derived from 1 and phosphonium chloride 2 in a twofold Wittig olefination, were converted with phosphonium bromides 4 to give the (all-E)-arylpolyenaldehydes 5 and 6. A terminal alkyl chain was introduced in dialdehydes 1a and 3a by reaction with P,P-didecyldibenzophospholium bromide 8, resulting in polyenals 9. Wittig olefination of 5c and 9a with phosphonium chloride 2 afforded the (2-thienyl)tridecahexaenal 7 and the docosahexaenal 10. With respect to monolayer formation on oxidized Si(100) surfaces, (9-anthryl)-and (2-thienyl)-w-functionalized polyenetriethoxysilanes 16 and 17 were prepared in a reaction sequence involving the introduction of a terminal triple bond with [3-(trimethylsilyl)prop-2-ynyl]triphenylphosphonium bromide (11), desilylation of the resulting arylpolyeninetrimethylsilanes 12, 13 with Bu 4 NF×3H 2 O, and subsequent hydrosilylation of the arylpolyenines 14, 15 using triethoxysilane under dichlorocyclooctadienylplatinum(II) catalysis.In donor-acceptor-substituted conjugated polyenes and oligothiophenes a quantitative energy transfer from the photoexcited donor, for example anthracene, to the acceptor, for example tetraphenyl porphyrin, could be proved by fluorescence spectroscopy. 2-6 Replacement of the porphyrin in these supermolecules by stronger electron acceptors such as fullerene, pyridines or pyridinium moieties, respectively, enables an uni-directed intramolecular electron transfer from the photoexcited anthracene donor to the respective acceptor. 7-9 In contrast to the energy transfer mentioned above, the electron transfer in these conjugated p-systems can already be interrupted by a methylene group as saturated spacer. This offers the possibility of incorporating, for example, photochemically switchable organic molecules 10 in donor-acceptor substituted conjugated p-systems in order to realize suitable components for electronic devices on a molecular level. Any application of the described isolated molecules as components in "molecular electronics , however, requires the formation of supramolecular structures, for example well-ordered monomolecular layers and bonding of the molecular building blocks to existing information systems (e.g., microelectronic silicon components). Anthracene-polyene pyridinium compounds have been investigated first with respect to such kind of ordering of single molecules. 11,12 As amphiphiles these compounds are able to form ordered monolayers on the water/air surface which are transferable onto solid supports (e.g. glass) by the Langmuir-Blodgett technique. The labile bonding of these functionalized monolayers to the solid support is a crucial disadvantage for possible applications of LB films in "molecular electronics . We have therefore ...

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Synthesis of Aryl-Terminated Polyenaldehydes and Polyenetriethoxysilanes for Preparation of Self-Assembled Monolayers on Silicon Surfaces

Effenberger¹,

Wezstein²

2001

Synthesis

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Synthesis of Conjugated Dienes and Polyenes

Mehta

Rao

2009

Patai's Chemistry of Functional Groups

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Introduction Elimination Reactions Addition–Elimination Reactions Concerted Reactions W ittig and Related Reactions Coupling Reactions From Alkynes From Heterocyclic Compounds Miscellaneous Acknowledgements

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Carbon–Carbon Bond Formation

Sheldon

Bekkum

2000

Fine Chemicals Through Heterogeneous Catalysis

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Herstellung konjugierter Polyene mit Anthryl- undN-Methylpyridinium- Endgruppen

Cited by 13 publications

References 0 publications

Synthesis of Aryl-Terminated Polyenaldehydes and Polyenetriethoxysilanes for Preparation of Self-Assembled Monolayers on Silicon Surfaces

Synthesis of Aryl-Terminated Polyenaldehydes and Polyenetriethoxysilanes for Preparation of Self-Assembled Monolayers on Silicon Surfaces

Synthesis of Conjugated Dienes and Polyenes

Carbon–Carbon Bond Formation

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