Polydiacetylenes

Zuilhof, Han; Barentsen, Helma M.; Dijk, M. van; Sudhölter, Ernst J. R.; Hoofman, R.J.O.M.; Siebbeles, Laurens D. A.; Haas, Matthijs P. de; Warman, John M.

doi:10.1016/b978-012513904-5/50006-5

Cited by 32 publications

(54 citation statements)

References 425 publications

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“…This value is still significantly lower than the reported values for longer-wavelength absorptions (l max up to 700 nm) of PDA chains, the most closely related class of conjugated polymers. [29] For plots like these, it is known that for extended oligomers they start to deviate from linearity, and curve horizontally near the yaxis. [30,31] This was previously observed for the highly analogous oligo-triacetylenes (OTAs), [28] for which truncation effects on the conjugation are already noticeable for the oligomers with more than 24 conjugated bonds.…”

Section: Steady-state Absorption In Solutionmentioning

confidence: 97%

“…This tendency is in line with the observation that PDA polymers show marginal fluorescence quantum yields, mostly lower than 0.001. [29,38] Fluorescence lifetimes and anisotropy: Picosecond time-resolved single photon counting with l ex = 372 nm was used to determine the fluorescence lifetimes (t F ) of the oligomers series 1-n. The observed lifetimes in the HODA series measured in n-hexane are shown in Table 4.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

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Synthesis and Optoelectronic Properties of Nanometer‐Sized and Highly Soluble Homocoupled Oligodiacetylenes

Pilzak¹,

Baggerman²,

Lagen³

et al. 2009

Chemistry A European J

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A new series of pure, nanometer-sized and highly-soluble homocoupled oligodiacetylenes (HODA) consisting of two symmetrical oligodiacetylene units was synthesized with high yield and on a multi-milligram scale under mild, catalytic Sonogashira conditions. The lambda(max) and the epsilon(max) of absorption for these HODAs show an increase with the chain elongation. The lambda(max) converges to 450 nm for the longest members of the series at micromolar concentration and to 462 nm for thin drop-casted films. An additional red-shifted absorption is observed in the solid state and in solution at low temperatures, which is caused by aggregation. The lambda(max) of the fluorescence emission increases with the chain length and reaches 492 nm for the longest oligomer. The fluorescence quantum yield has its maximum for the shortest oligomer and decreases rapidly for the longer ones. A similar trend is found for the fluorescence lifetime with a maximum of 100 ps for the homocoupled monomer. The rotational correlation time shows a linear increase with the oligomer length. This reveals a significant persistence length and indicates that the HODA molecules are fully stretched molecular rods (up to 8.2 nm).

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Section: Steady-state Absorption In Solutionmentioning

confidence: 97%

Section: Wwwchemeurjorgmentioning

confidence: 99%

Synthesis and Optoelectronic Properties of Nanometer‐Sized and Highly Soluble Homocoupled Oligodiacetylenes

Pilzak¹,

Baggerman²,

Lagen³

et al. 2009

Chemistry A European J

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“…-10 K3 lower perpendicular to it (Zuilhof et al 2001). However, this value refers to macroscopic samples.…”

Section: K2mentioning

confidence: 99%

What determines the mobility of charge carriers in conjugated polymers?

Laquai

Wegner

Bäßler

2007

Phil. Trans. R. Soc. A.

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In a conjugated polymer, the mobility of charge carriers is not a well-defined coefficient of a particular material as it is in an inorganic crystalline semiconductor but depends on the time domain of detection. On a time-scale of typically 100 fs, the on-chain mobility is ultra-high and controlled by the electronic band width of the polymer chain. When a carrier hits a chain imperfection, subsequent mesoscopic on-chain motion is retarded and controlled by intrachain disorder to which the chain environment contributes. Macroscopic transport commences after a time when interchain carrier jumps become rate limiting. It is routinely probed by time-of-flight experiments and can be rationalized in terms of random walk within a rough energy landscape. Experimental signatures of the various modes of transport are discussed.

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“…This color change is one piece of evidence for topochemical polymerization of diyne compounds, as has been reported in literature. [32][33][34][35] In addition to coloring, a small change in the X-ray powder diffraction profile was also observed; the d-value changed from 56.5 Å before γ-radiation to 55.8 Å after the reaction. A similar but slightly smaller d-value of the polymer crystal after γ-ray irradiation supports the topochemical polymerization, being the same as the behavior of other diene and diyne polymerizations.…”

Section: Resultsmentioning

confidence: 96%

Organic Intercalation of Unsaturated Amines into Layered Polymer Crystals and Solid-State Photoreactivity of the Guest Molecules in Constrained Interlayers

Matsumoto

Fujioka

Kunisue

2003

Polym J

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ABSTRACT:We have investigated the intercalation of several unsaturated amines using poly(muconic acid) crystals as the layered organic polymer host. Allyl-and oleylamines are intercalated into the polymer crystals in order to introduce an olefin moiety in the side chain of poly(muconic acid). The oleylammonium polymer crystals are alternatively obtained by the topochemical polymerization of oleylammonium muconate as the corresponding ammonium monomer crystals under photoirradiation in the crystalline state, while the photoirradiation of the allylammonium muconate crystals results in the formation of isomers. The inner double bond of the intercalated oleyl group has a low reactivity under UV irradiation, and the allyl group has no reactions. In contrast, diene and diyne moieties introduced into the side chain by the intercalation using 2,4-hexadienyl-, 2,4-tetradecyldienyl-, and 10,12-pentacosadiynylamines as the guest amines readily react to give a new type of the polymer crystal consisting of alternately stacked polymer nano-sheets. We have revealed that the intercalation of long-chain unsaturated amines proceeds in a high conversion, and the photoreactivity of the unsaturated functional groups in the side chain is determined by the kind of unsaturated groups and the stacking distance of the amine molecules in the layers.KEY WORDS Layered Polymer Crystals / Intercalation / Poly(muconic acid) / Solid-State Photoreaction / Polydiacetylene / Organic/inorganic nano-composites with an organized structure have attracted interests in the fundamental and applied fields of polymer chemistry and nanomaterial science. 1-3 A large number of inorganic solids with a two-dimensional structure such as clays, metal phosphonates or phosphites, graphite, and metal oxides have been reported, 4, 5 and the properties and functions of these layered materials are modified by combination with organic molecules as the guest compounds. [6][7][8][9][10][11] The combination of materials with a different nature efficiently induces a new property and function, which cannot be attained from an organic or inorganic compound alone. The structure and properties of the composites consisting of various types of clays and polymers have also been investigated. [12][13][14][15] In contrast to a large number of studies on intercalation systems made of inorganic compounds or inorganic-organic hybrids, very few examples are known as an intercalation system consisting of organic compounds as both the host and guest. [16][17][18][19][20][21] We have previously demonstrated the fundamental features and mechanism of the intercalation of various alkylamines into poly(muconic acid) (PMA) as the organic host compound 21-24 (Scheme 1). Long-chain alkylamines are suitable as the guest molecules and the intercalation provides a new layered polymer crystal with an interlayer spacing different from that of the original PMA crystals. The organic intercalation system consisting of layered organic polymers and organic guest amines has some characteristics different fr...

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Polydiacetylenes

Cited by 32 publications

References 425 publications

Synthesis and Optoelectronic Properties of Nanometer‐Sized and Highly Soluble Homocoupled Oligodiacetylenes

Synthesis and Optoelectronic Properties of Nanometer‐Sized and Highly Soluble Homocoupled Oligodiacetylenes

What determines the mobility of charge carriers in conjugated polymers?

Organic Intercalation of Unsaturated Amines into Layered Polymer Crystals and Solid-State Photoreactivity of the Guest Molecules in Constrained Interlayers

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