Preparation of polydiacetylene single crystals based on physical vapor growth technique

Jo, Sadaharu; Yoshikawa, Hitoshi; Fujii, Akane; Takenaga, Mitsuru

doi:10.1016/j.synthmet.2005.01.028

Cited by 15 publications

(16 citation statements)

References 12 publications

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“…[33,34] Moreover, PDAs are unique due to their formation by topochemical polymerization from crystalline diacetylenes, [35] resulting in quasi one-dimensional organic quantum wires. [31,36,37] During this process PDA chains are formed in the presence of neighboring parallel conjugated backbones. Although this may give PDAs some of their unique properties, it also blurs the distinction between intrachain and inter-chain effects.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Properties of all‐trans‐Oligodiacetylenes

Pilzak

Lagen

Hendrikx

et al. 2008

Chemistry A European J

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A new series of pure and highly soluble oligodiacetylenes (ODAs) was synthesized in high yield and on a multi-milligram scale by a sequence of Sonogashira reactions with a strongly reduced level of homocoupling. The lambda max and epsilon max of these ODAs show an increase with both chain elongation and solvent polarity. A plot of lambda max absorption versus 1/CL (CL=conjugation length) was shown to be linear. The lambda max converges to 435 nm for the longest members of the series at micromolar concentration. This reveals that the longest wavelength absorption observed for PDA chains (lambda max up to 700 nm) is due to aggregation effects. The fluorescence quantum yield increased from monomer to trimer and decreased for longer ODAs. A similar trend is found for the lifetime of fluorescence with a maximum of 600 ps for the trimer. The observed linearity of the rotational correlation time with the oligomer length implies that the ODA chains in solution lack significant geometrical changes. This implies that the ODAs in solution are fully stretched molecular rods of up to 4 nm in length.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Properties of all‐trans‐Oligodiacetylenes

Pilzak

Lagen

Hendrikx

et al. 2008

Chemistry A European J

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“…This lack of study is a shortcoming given several of the unique properties of polydiacetylenes, such as nonlinear optical (NLO) properties and chromic properties, that arise due to its p-conjugated system. [4,[29][30][31][32][33][34] Furthermore, few examples of the structural modulation of such p-oligomeric chains by incorporation of an aromatic moiety are reported. [35][36][37] Such an approach provides a new and versatile way to explore and optimize the optoelectronic properties of conjugated oligomers.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Conjugated Organic Oligomers Consisting of Oligodiacetylene and Thiophene Units: Synthesis and Optical Properties

Pilzak

Gruijthuijsen

Doorn

et al. 2009

Chemistry A European J

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Novel and highly soluble hybrid conjugated organic oligomers consisting of oligodiacetylene and thiophene units have been synthesized in high purity through iterative and divergent approaches based on a sequence of Sonogashira reactions. The series of thiophene-containing oligodiacetylenes (ThODAs) and homocoupled ThODAs (HThODAs) show--both in solution and in the solid state--a strong optical absorption, which is progressively red shifted with increasing chain length. The linear correlation of the absorption maximum (lambda(A)(max)) with the inverse of conjugation length (CL = number of double and triple bonds) shows that the effective conjugation length of this system is extended up to at least CL = 20. Furthermore, absorption measurements of dropcast thin films display not only a bathochromic shift of the absorption maxima but also a higher wavelength absorption, which is attributed to increased pi-pi interactions. The wavelength of the maximum fluorescence emission (lambda(E)(max)) also increases with CL, and emission is maximal for oligomers with CL=7-12 (fluorescence quantum yield Phi(F) = approximately 0.2). Both longer and shorter oligomers display marginal emission. The calculated Stokes shifts of these planar materials are relatively large (0.4 eV) for all oligomers, and likely due to excitation to the S(2) state, thus suggesting that the presence of enyne moieties dominates the ordering of the lowest excited states. The fluorescence lifetimes (tau(F)) are short (tau(F,max) =<<1 ns) and closely follow the tendency obtained for the fluorescence quantum yield. The anisotropy lifetimes show a near-linear increase with CL, in line with highly rigid oligomers.

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“…Many diacetylene (DA) monomer single crystals were obtained by the PVT technique [13]. A schematic drawing of the horizontally arranged furnace used for the PVT technique is shown in Fig.…”

Section: Methodsmentioning

confidence: 99%

“…Since Karl's pioneering work [10], the physical vapor transport (PVT) technique has been developed to obtain high-quality organic single crystals, mainly by Laudise et al [11] and Kloc et al [12]. Recently, a type of PDA single crystal has been grown by the PVT technique [13]. This PDA single crystal is expected to contain a smaller amount of impurity, because its composites are separated during crystal growth owing to the vapor pressure difference between the source material and impurities.…”

Section: Introductionmentioning

confidence: 99%