Organic Nanofibers from Chloride-Functionalized <i>p</i>-Quaterphenylenes

Schiek, Manuela; Lützen, and Arne; Al‐Shamery, Katharina; Balzer, Frank; Rubahn, Horst‐Günter

doi:10.1021/cg060192v

Cited by 31 publications

(21 citation statements)

References 36 publications

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“…Unfortunately, the compound does not lend itself easily to chemical modifications, because of its low solubility. Functionalization has thus been achieved on quaterphenyl (17) (Brewer et al, 2006;Schiek et al, 2006;Schiek et al, 2007). Another strategy is to dope the nanofibers p-hexaphenyl with α-hexathiophene (18).…”

Section: Nanofibers Made Of Low-molecular-weight Molecules Without Apmentioning

confidence: 99%

Organic Fluorescent Nanofibers and Sub-Micrometer Rods

Fery–Forgues¹,

Fournier‐Noël²

2010

Nanofibers

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Section: Nanofibers Made Of Low-molecular-weight Molecules Without Apmentioning

confidence: 99%

Organic Fluorescent Nanofibers and Sub-Micrometer Rods

Fery–Forgues¹,

Fournier‐Noël²

2010

Nanofibers

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“…7 In the broad spectrum of available material systems, the epitaxial growth of molecular assemblies on various substrates has been thoroughly investigated and identified as a promising basis for numerous device applications in the field of organic electronics. In this context, the growth of rodlike organic molecules on muscovite mica substrates has been extensively studied [9][10][11][12][13][14] and, in particular, phenylenes have been recognized as key materials for a large number of optical applications, e.g., lasing and wave guiding, 15 due to their advantageous ability to form highly parallel organic nanofibers. To broaden the spectrum of optical applications the phenylene oligomers should be substituted by other rodlike molecules, e.g., acenes or thiophenes, 3,13 which presupposes a detailed knowledge concerning epitaxial growth.…”

Section: Introductionmentioning

confidence: 99%

Epitaxial growth of sexithiophene on mica surfaces

et al. 2011

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We present a systematic study on the epitaxial growth of α-sexithiophene (6T) on two different types of substrates, phlogopite and muscovite mica. The study is based on a structural and morphological analysis using specular x-ray diffraction, x-ray diffraction pole figure technique, transmission electron microscopy, atomic force microscopy, and optical microscopy. It is shown, that 6T molecules on mica substrates crystallize in two different configurations, characterized either by the (411) or (100) contact plane. Whereas the first orientation consists of needle-like structures, the latter one forms an island-like morphology, and both crystal orientations exhibit a well-defined relationship with respect to each other. We demonstrate that this finding can be explained by directed epitaxy of islands along the sidewalls of the needle-like structures.

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“…Di-Chloro-p-Quaterphenylene (CLP4) [5,6] Vapour deposition of CLP4 on muscovite mica leads to formation of mutually aligned nanostructures. In a fluorescence microscope they emit polarised blue light after excitation with UV light from a high-pressure mercury lamp (Fig.4.7).…”

Section: 22mentioning

confidence: 99%

“…The black bars correspond to a nominal film thickness of 2nm, the grey bars to 9 nm of deposited CLP4. From [5].…”

Section: 22mentioning

confidence: 99%

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Organic Molecular Nanotechnology

Schiek

Balzer

Al‐Shamery

et al. 2008

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Zur Homepage der Dissertation AbstractFormation of needle-like crystals from inorganic as well as from organic semiconductors such as para-phenylenes, α-thiophenes and phenyl-thiophene co-oligomers on dielectric surfaces has attracted increasing interest within the last years. The para-hexaphenylene has proven to be a versatile building block for generating long, parallely aligned organic nanofibers by a self-assembly process on a muscovite mica substrate via sublimation in high vacuum. These nanofibers possess outstanding optical properties like strong, polarised blue fluorescence in high quantum yields after unpolarised excitation with UV light, waveguiding and lasing features. Furthermore, they are chemically and thermically stable and can be easily detached from the growth substrate to serve as key elements in next generation optoelectronic and nanophotonic devices. Owing to their typical height and width on a nanometer scale and length up to one millimeter, the fibers bridge the gap between microscopic and macroscopic dimensions. The morphology of the nanofibers (length, height, width, aspect ratio, bending into rings) is susceptable to process parameters and pretreatment of the substrate. But chemically functionalisation of the molecular building block as key step of this thesis widens the scope of possibilities: Nanoaggregates with tailored morphology and optical properties are generated from designed functionalised molecular building blocks. Functional groups have been implemented at the 1,4´´´-para-positions of p-quaterphenylenes using a non-trivial Suzuki cross-coupling strategy. Symmetrically as well as non-symmetrically functionalised oligomers have been achieved in excellent yields and high purity. Additionally, the synthesis of phenyl-thiophene cooligomers and their acceptability for the nanofiber growth on muscovite mica via organic molecule deposition in high vacuum are presented. The fluorescence peak emission frequency of the nanostructures from the substituted p-quaterphenylenes shifts within the blue depending on the functionalisation. While dimensions are still influenced by the growth parameters, the overall shape (i.e. cross-section) of the aggregates alters significantly with the functional group. Even new properties like nonlinear optical activity are accessible. Due to intrinsic nonzero hyperpolarisability of push-pull functionalised oligomers, the respective nanofibers act as frequency doublers and emit strong second harmonic light after excitation with near infrared femtosecond laser pulses. Note that this design approach is possible while conserving the concept of highly crystalline nanofibers. Thus, a new route of bottom-up nanotechnology is presented starting from organic molecular synthesis towards generating of tailormade organic nanofibers opening new prospects for future nanotechnology. 3 ZusammenfassungDie Bildung von nadelförmigen Kristallen aus anorganischen und organischen Halbleitermolekülen wie zum Beispiel para-Phenylenen, α-Thiophenen und Phenylthiophen Co-oligomeren fa...

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Organic Nanofibers from Chloride-Functionalized p-Quaterphenylenes

Cited by 31 publications

References 36 publications

Organic Fluorescent Nanofibers and Sub-Micrometer Rods

Organic Fluorescent Nanofibers and Sub-Micrometer Rods

Epitaxial growth of sexithiophene on mica surfaces

Organic Molecular Nanotechnology

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