Electronic structure and circular dichroism spectroscopy of naphthalenediimide nanotubes

Bulheller, Benjamin M.; Pantoş, G. Dan; Sanders, Jeremy K. M.; Hirst, Jonathan D.

doi:10.1039/b905187b

Cited by 32 publications

(32 citation statements)

References 32 publications

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“…The radical anions comprise of characteristic visible and near‐infrared absorption bands at >450 nm. The chiral supramolecular assemblies of NDIs exhibit strong exciton‐coupled circular dichroism (CD) 15. The negative sign of the first cotton effect is ascribed to M‐type of helicity while the positive sign of the first cotton effect to P‐type of helicity.…”

Section: Amino Acid Derivatized Ndismentioning

confidence: 99%

Amino Acid Derivatized Arylenediimides: A Versatile Modular Approach for Functional Molecular Materials

Avinash

Govindaraju

2012

Advanced Materials

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Nature's elegant molecular designs and their assemblies with specific structure-property correlations have inspired researchers to design and develop bio-mimics for advanced functional applications. To realize such advanced molecular materials, naturally evolved amino acids are arguably the ideal auxiliaries due to their remarkable molecular/chiral recognition and distinctive sequence specific self-assembling properties. Over the years, this modular approach of derivatizing naphthalenediimides (NDIs) and perylenediimides (PDIs) with amino acids and peptides have resulted in several hitherto unknown molecular assemblies with phenomenal impact on their performance. Derivatization with versatile arylenediimides is especially interesting due to their wide spread applications in fields ranging from biomedicine to electronics. Herein some of these seminal reports of this rapidly emerging field and the design principles embraced are discussed.

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Section: Amino Acid Derivatized Ndismentioning

confidence: 99%

Amino Acid Derivatized Arylenediimides: A Versatile Modular Approach for Functional Molecular Materials

Avinash

Govindaraju

2012

Advanced Materials

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“…The region spanning 300-400 nm in the CD spectra corresponds to transitions polarized along the long axis of the NDI chromophore, and is correlated with the intermolecular helical twist-sense relating adjacent p stacked NDI units. [18] Accordingly, the positive amplitude of the CD trace in this region indicates an intermolecular P-type NDI orientation within the nanotubes formed from A. In contrast, the inverted nature of the CD peaks in this region, reflect M-type helical packing for B and C.…”

mentioning

confidence: 93%

Aqueous Self‐Assembly of L‐Lysine‐Based Amphiphiles into 1D n‐Type Nanotubes

Shao¹,

Gao²,

Kim³

et al. 2011

Chemistry A European J

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We prepared novel semi‐interpenetrating polymer network (semi‐IPN) materials by mixing poly(ester urethane), synthesized by the polymerization reaction between poly(ethylene glycol adipate) and toluene diisocyanate in the presence of 2,2‐bis(hydroxyl methyl) propionic acid as an extender, with nitrokonjac glucomannan (NKGM) in tetrahydrofuran and then by crosslinking and curing the mixture at 60°C for 1.5 h. Miscibility and the properties of the sheets were studied by Fourier transition infrared spectroscopy, wide‐angle X‐ray diffraction, differential scanning calorimetry (DSC), and scanning electron microscopy. The results indicate that strong interactions between poly(ester urethane) and NKGM in the semi‐IPN sheets occurred, leading to good miscibility between the two polymers in the whole region of component ratios. When the content of NKGM was 10%, the tensile strength and breaking elongation of the semi‐IPN sheet were simultaneously enhanced to 35 MPa and 960%, respectively, compared with pure polyurethane. The DSC curves showed a low softening temperature for the poly(ester urethane), which resulted in the high elongation. By changing the NKGM amount from 10 to 90%, we prepared a series of composite materials from an elastomer to tough plastics. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 90: 2224–2228, 2003

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“…[58] The NDI supramolecular nanotubes which have cavities with diameters in the range of 1-2 nm created by hydrogen bonding have been shown to act as receptors for aromatic molecules including naphthalene-based guests or fullerenes. [59,60] Fluorescence imaging studies on fluorescent carbon nanotubes have thus far focused primarily on the measurement of the steady state spatial changes in emission intensity or wavelength. [4,[15][16][17][18][19]21,23,[61][62][63][64][65][66][67][68] The use of fluorescence lifetime imaging microscopy (FLIM) in combination with multiphoton excitation and near infrared (NIR) femtosecond laser pulses is widely used in the study of small molecule fluorophores particularly for in vitro studies.…”

Section: Introductionmentioning

confidence: 99%

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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Electronic structure and circular dichroism spectroscopy of naphthalenediimide nanotubes

Cited by 32 publications

References 32 publications

Amino Acid Derivatized Arylenediimides: A Versatile Modular Approach for Functional Molecular Materials

Amino Acid Derivatized Arylenediimides: A Versatile Modular Approach for Functional Molecular Materials

Aqueous Self‐Assembly of L‐Lysine‐Based Amphiphiles into 1D n‐Type Nanotubes

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

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