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Grummt, U.‐W.; Birckner, Eckhard; Al-Higari, M.; Egbe, Daniel Ayuk Mbi; Klemm, Elisabeth

doi:10.1023/a:1016647632179

Cited by 17 publications

(12 citation statements)

References 14 publications

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“…Therefore, the photophysical properties of the ligand system 5,5 0 -bisphenyletynyl-2-2 0 -bipyridine (1) [19,20] and of the closely related 4,4 0 -substituted phenyleneethynylene based bipyridine derivatives [21] have already been characterized to some extent. In this context, the novel compounds 2 and 3 reported here can be considered as useful monomeric model species for studying the intrinsic spectroscopic features of organometallic poly-aryleneethynylene polymers containing functional rhenium or rhodium sites.…”

Section: Introductionmentioning

confidence: 99%

Luminescence and spectroscopic studies of organometallic rhodium and rhenium multichromophore systems carrying polypyridyl acceptor sites and phenylethynyl antenna subunits

Oppelt

Egbe

Monkowius

et al. 2011

Journal of Organometallic Chemistry

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Section: Introductionmentioning

confidence: 99%

Luminescence and spectroscopic studies of organometallic rhodium and rhenium multichromophore systems carrying polypyridyl acceptor sites and phenylethynyl antenna subunits

Oppelt

Egbe

Monkowius

et al. 2011

Journal of Organometallic Chemistry

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“…Examination of the effect of the degree of polymerization suggested that an effective -conjugation length for the radiation process was a one or two repetition unit. Copolymers of phenanthroline 3,8-diyl (106-108) were also reported [77].…”

Section: Extended Oligopyridinesmentioning

confidence: 96%

Fluorescent Oligopyridines and their Photo-Functionality as Tunable Fluorophores

Mutai¹,

Araki

2007

COC

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Oligopyridines connected through the 2-and 6-positions have long been the subject of continuing interest because of their high ability to interact with metal ions and/or other molecules, and their transition-metal complexes have been intensely studied for decades because of their characteristic photophysical properties. However, relatively few have been known in regard to the photophysical and photo-functional properties of oligopyridine derivatives. From the late 1990s, fluorescent oligopyridines have been of considerable interest as tunable fluorophores by intermolecular interaction, and the design and synthesis of novel oligopyridine derivatives and their application to fluorescent sensors has increasingly been studied. In this article, we will review recent developments of fluorescent oligopyridines and their photo-functionality.

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“…[30,31] For polymers 30 and 33 it is possible to make a direct comparison between the classical and the EOP procedures outlined in Route a and Route d of Figure 10. Starting in both case from 1,4-diiodo-2,5-bis(octyloxy)-benzene [34, Ar ¼ 2,5-bis(octyloxy)benzene], Grummt [32] and Weder [20e] first prepared the 1,4-bis(trimethylsilyl)ethynyl-2,5-bis(octyloxy)benzene [36, Ar ¼ 2,5-bis(octyloxy)benzene] and then by removal of the TMS protecting groups formed the 1,4-bis(ethynyl)-2,5-bis(octyloxy)benzene [37, Ar ¼ 2,5-bis(octyloxy)benzene]. This was subsequently coupled with 6 and 9 to form 30 [32] and 33, [20e] respectively.…”

Section: Comparison Of Eop Synthetic Protocol and Current Procedures mentioning

confidence: 99%

“…Starting in both case from 1,4-diiodo-2,5-bis(octyloxy)-benzene [34, Ar ¼ 2,5-bis(octyloxy)benzene], Grummt [32] and Weder [20e] first prepared the 1,4-bis(trimethylsilyl)ethynyl-2,5-bis(octyloxy)benzene [36, Ar ¼ 2,5-bis(octyloxy)benzene] and then by removal of the TMS protecting groups formed the 1,4-bis(ethynyl)-2,5-bis(octyloxy)benzene [37, Ar ¼ 2,5-bis(octyloxy)benzene]. This was subsequently coupled with 6 and 9 to form 30 [32] and 33, [20e] respectively. In both cases overall yields are acceptable (60 -70%), however these procedures require isolation and purification of both the TMS (36) and the terminal alkyne (37) intermediates.…”

Section: Comparison Of Eop Synthetic Protocol and Current Procedures mentioning

confidence: 99%

Use of the Pd-PromotedExtended One-Pot (EOP) Synthetic Protocol for the Modular Construction of Poly-(arylene ethynylene)co-Polymers [?Ar?C?C?Ar??C?C?]n, Opto- and Electro-Responsive Materials for Advanced Technology

Micozzi

Ottaviani

Giardina

et al. 2005

Advanced Synthesis & Catalysis

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Abstract:We report on the use of our novel multistep/ one-pot/Pd-promoted synthetic strategy, named extended one-pot (EOP), for the preparation of polymeric conjugated systems characterized by a backbone composed of regularly alternating alkyne and arylene moieties of type [ À C C À A À C C À B À ] n . The "A" unit (or module) is in charge of impressing mechanical strength, chemical stability and processability to the polymer, while different "B" units (or modules) have been selected to obtain polymers with different functional properties. With this "modular approach" concept, a series of co-poly(arylene ethyny-Ar' ¼ 1,10-phenanthroline, hydroquinone, pyridine, tetrafluorobenzene, dithiophene, benzene, and anthracene] potentially useful for the fabrication of sensory, electroactive and light-emitting materials, have been formed. Investigations of the photophysical properties of these materials, both in solution and in the solid state, have demonstrated a large degree of variation of properties depending on the nature of Ar' and the extension of the conjugation in the polymeric backbone. This EOP synthetic protocol, with its multiple and sequential one-pot Pd-catalyzed processes, is characterized by a very low catalyst charge loading, a consistent cut-down of reaction times, ease of operation and cost with respect to conventional procedures to obtain ethynylated polymers. Moreover, although it is based on the Pd-catalyzed coupling of organostannanes and aromatic halides (Stille reaction), the EOP synthetic route optimizes and reduces the use of tin, because during the multi-step one-pot process, tin intermediates are in situ formed by complete reconversion of tin by-products generated in the course of the transformation. In addition, after formation and isolation of polymeric materials, tin-containing products are recovered and reused to form new reagents for the delivery of the alkyne moiety into the polymer backbone.

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Cited by 17 publications

References 14 publications

Luminescence and spectroscopic studies of organometallic rhodium and rhenium multichromophore systems carrying polypyridyl acceptor sites and phenylethynyl antenna subunits

Luminescence and spectroscopic studies of organometallic rhodium and rhenium multichromophore systems carrying polypyridyl acceptor sites and phenylethynyl antenna subunits

Fluorescent Oligopyridines and their Photo-Functionality as Tunable Fluorophores

Use of the Pd-PromotedExtended One-Pot (EOP) Synthetic Protocol for the Modular Construction of Poly-(arylene ethynylene)co-Polymers [?Ar?C?C?Ar??C?C?]n, Opto- and Electro-Responsive Materials for Advanced Technology

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