Controlled Self-Assembly of Triphenylene-Based Molecular Nanostructures

Duzhko, Volodimyr V.; Shi, Hefei; Singer, Kenneth D.; Semyonov, Alexander N.; Twieg, Robert J.

doi:10.1021/la060763l

Cited by 22 publications

(31 citation statements)

References 25 publications

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“…This suggests an aggregation of the triphenylene moieties in the lm. 55,56 In contrast, lm and diluted DCM solution of the triad show similar features regarding the absorption bands of the triphenylene units. Triphenylene units are therefore poorly interacting along the differentiated columns of the triad as along the mixed dyad columns, which is easily understandable considering the peculiar geometry and stacking behaviour of the species.…”

Section: Absorption and Steady-state Uorescence Emission Spectra In mentioning

confidence: 95%

Structure–charge transfer property relationship in self-assembled discotic liquid-crystalline donor–acceptor dyad and triad thin films

et al. 2016

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The photophysical properties of donor-acceptor (D-A) and donor-acceptor-donor (D-A-D) liquid crystalline dyads and triads based on two different discotic mesogens are examined in thin films by steady-state optical spectroscopy and subpicosecond transient absorption measurements. In these systems, triphenylene and perylene bisimide units are covalently linked by flexible decyloxy chain(s) and act as an electron donor (D) and acceptor (A), respectively. These discotic liquid-crystalline systems form well-separated D and A p-stacked columnar structures in thin films. The absorption spectra of the films indicate an aggregation of the perylene bisimide and triphenylene moieties along the columns. Steadystate photoluminescence measurements show a strong fluorescence quenching that is mainly attributed to a photo-induced charge transfer process taking place between the triphenylene and perylene bisimide units. Subpicosecond transient absorption measurements show that the photoinduced charge transfer (CT) states in the dyad and triad films are formed within 0.3 ps and recombine on a 150-360 ps time scale. In addition, a correlation between the dynamics of the charge recombination process and the spacing distances between D and A units can be established in the dyad and triad films. This study provides important information on the relationship between molecular packing and the charge transfer properties in such self-organized D and A columnar nanostructures.

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Section: Absorption and Steady-state Uorescence Emission Spectra In mentioning

confidence: 95%

Structure–charge transfer property relationship in self-assembled discotic liquid-crystalline donor–acceptor dyad and triad thin films

et al. 2016

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“…Triphenylene and phthalocyanine derivatives selfassemble out of solution into fibers with well-defined internal structure and controlled external geometry. 202,203 Floating phthalocyanine fibers in dodecane solution have been shown to adhere in a planar way to an ITO substrate in the absence of an electric field. When the electric field is turned on, the fibers ''stand up'' with their long axes oriented in the direction parallel of the electric field.…”

Section: Tubes and Fibersmentioning

confidence: 99%

Discotic liquid crystals: a new generation of organic semiconductors

2007

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Discotic (disc-like) molecules typically comprising a rigid aromatic core and flexible peripheral chains have been attracting growing interest because of their fundamental importance as model systems for the study of charge and energy transport and due to the possibilities of their application in organic electronic devices. This critical review covers various aspects of recent research on discotic liquid crystals, in particular, molecular design concepts, supramolecular structure, processing into ordered thin films and fabrication of electronic devices. The chemical structure of the conjugated core of discotic molecules governs, to a large extent, their intramolecular electronic properties. Variation of the peripheral flexible chains and of the aromatic core is decisive for the tuning of self-assembly in solution and in bulk. Supramolecular organization of discotic molecules can be effectively controlled by the choice of the processing methods. In particular, approaches to obtain suitable macroscopic orientations of columnar superstructures on surfaces, that is, planar uniaxial or homeotropic alignment, are discussed together with appropriate processing techniques. Finally, an overview of charge transport in discotic materials and their application in optoelectronic devices is given.

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“…[10] However, to date, although a number of triphenylene-based small molecules and polymers have been designed and investigated, the high tendency towards selfassociation of triphenylene often leads to a dramatic decrease in fluorescence intensity, owing to their strong p-p stacking interactions. [11] To our knowledge, dendrimers based exclusively on interlinked triphenylene units have not been realized, probably as a result of the challenges associated with functionalized triphenylene derivatives serving as branching reagents in dendrimer and hyperbranched polymer synthesis. In this study, triphenylene is incorporated as a building block for the dendritic systems G1 (Scheme 1), G2, and G3 (Scheme 2).…”

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confidence: 99%