Soluble derivatives of perylene and naphthalene diimide for n-channel organic field-effect transistors

Singh, Tapender; Erten, Sinan; Güneş, Serap; Zafer, Ceylan; Turkmen, Gulsah; Kuban, B.; Teoman, Yildirim; Sariciftci, Niyazi Serdar; İçli, Sıddık

doi:10.1016/j.orgel.2006.06.010

Cited by 116 publications

(71 citation statements)

References 32 publications

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“…As stated above, the severe quenching of the fluorescence emission intensity was observed after adding SWNT (Figure 3c), indicating the strong absorption of the aromatic coating material onto the surface of the nanotube. [44] A red-shift in the emission maxima of NDI (20 nm) was also observed upon its anchoring onto SWNTs (Supplementary materials). The broadening in the UV-vis spectra as well as decay in the fluorescence emission intensity with time was observed, and this behavior stabilizes after 24 h presumably as the NDI absorption onto SWNTs reaches completion.…”

Section: Spectroscopic Investigations On the Ndi@swnt Compositementioning

confidence: 86%

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

Pantoş

Kuganathan

et al. 2011

Adv Funct Materials

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A new synthetic route to functionalized single walled carbon nanotubes (SWNTs) via supramolecular interactions using a specifically designed naphthalenediimide (NDI) nanoreceptor is demonstrated. The tendency of the NDI to spontaneously form composites with carbon nanomaterials leads to fluorescent amino acid tagged SWNTs, which are dispersible in widely accessible organic solvents (CHCl 3 , DMSO) as well as in biocompatible cell medium (EMEM, Eagle's modified essential medium). The X-ray crystal structure of the first iodine-tagged and amino acid-functionalized NDI molecule, designed especially to facilitate the high resolution transmission electron microscopy (HR TEM) imaging whilst retaining its ability to self-assemble into a nanodimensional receptor in weakly polar solvents, is also described. A new hybrid material, NDI@SWNT, was prepared and characterized as dispersed in organic solvents and aqueous media and in the solid state by HR TEM, tapping mode atomic force microscopy (TM AFM), scanning electron microscopy (SEM), circular dichroism, Raman and fluorescence spectroscopies (steady-state single and two-photon techniques). We have been interested in the design and spectroscopic investigation of new nanomaterials with light emitting properties.[67] The NDI nanotubular receptor recently developed [55] should have the ability to bind via donor-acceptor interactions to carbon nanomaterials, in an analogous manner to that found in the exciting new hybrids containing perylenes in SWNTselectron acceptor composites for photovoltaic applications, reported by the groups of Hirsch [12][13][14] and Guldi.[14]We report our investigations at the formation of a new nanohybrid, denoted NDI@SWNT, in solution and on a preparative scale. We report here for the first time, the recognition and coating of the aromatic surface of ultra-purified SWNTs (provided by Thomas Swan Ltd, Elicarb SWNTs, and further steampuriffied to ensure they are free of catalytic impurities or carbonaceous materials from the nanotube synthesis, Supplementary Information) by a new iodine-and amino acid-derivatized NDI. Investigations into the properties of the new material synthesized (in bulk and in dispersions in CHCl 3 , EtOH, DMSO and serum free aqueous cell culture media such as EMEM) have been carried out by Raman, circular dichroism, FT IR, UV-vis-NIR and fluorescence spectroscopies and imaged at the nanoscale by HR TEM, SEM, EDS and TM AFM. The cellular translocation of the resulting NDI@SWNT complex was investigated by a combination of fluorescence microscopy techniques including fluorescence lifetime imaging and cytotoxicity assays (MTT) in cancerous and non-cancerous cell lines. Here we have used such techniques to probe the integrity of a new nanocomposite denoted NDI@SWNT in vitro. Such an approach could aid the future understanding of the mechanism of action of supramolecular materials at the cellular level and improve the synthetic design of nanohybrids for biomedical imaging and therapeutic applications. Results and Discussions Synthe...

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Section: Spectroscopic Investigations On the Ndi@swnt Compositementioning

confidence: 86%

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

Pantoş

Kuganathan

et al. 2011

Adv Funct Materials

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“…1 2.4. Synthesis of perylene-3,4,9,10-tetracarboxylic diimide tetraester (4) A mixture of methyl acrylate (2.7 ml, 32 mmol) and 1.5 g of 3 (3.2 mmol) in 30 ml of methanol was stirred for 4 days at room temperature, then the precipitate was collected by filtration, washed with water and dried. The crude solid was extracted with boiling chloroform to give after vacuum evaporation of the solvent and silica-gel chromatography (methylene chloride) 0.74 g (28%) pure tetraester 4 as dark-red crystals (m.p.…”

Section: Synthesis Of Amino Functionalized Perylene-34910-tetracarmentioning

confidence: 99%

Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer

2011

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“…Due to their photo-physical and photo-chemical properties the 1,8-naphthalimide derivatives can be used as fluorescence dyes for solar energy collectors and photosynthesis under concentrated sunlight [12], fluorescent markers in biological cells [13] as well as laser active media [14][15][16]. Recently, naphthalimides have also found applications in organic thin film field-effect transistors (OFETs), integrated circuit, displays, memory cards, chemical and pressure sensors, smart price tags and labels [17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photophysical Characterizations of Thermal -Stable Naphthalene Benzimidazoles

2011

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Soluble derivatives of perylene and naphthalene diimide for n-channel organic field-effect transistors

Cited by 116 publications

References 32 publications

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

Interactions Between Amino Acid‐Tagged Naphthalenediimide and Single Walled Carbon Nanotubes for the Design and Construction of New Bioimaging Probes

Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer

Synthesis and Photophysical Characterizations of Thermal -Stable Naphthalene Benzimidazoles

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