Naphthalenebisimides as photofunctional surfactants for SWCNTs – towards water-soluble electron donor–acceptor hybrids

Dirian, Konstantin; Backes, Susanne; Backes, Claudia; Strauß, Volker; Rodler, Fabian; Hauke, Frank; Hirsch, Andreas; Guldi, Dirk M.

doi:10.1039/c5sc02944a

Cited by 13 publications

(15 citation statements)

References 75 publications

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“…In addition to -CN, many other electron-withdrawing groups like perylene [57][58][59] derivatives have been introduced into the polymer main chain and directly immobilized onto the SWCNT surface to form well-dispersed suspensions [44]. A perylenediimide (PDI) acceptor containing chiral polymer (S-PBN(b)-Ph 4 PDI) dispersed (6, 5) chirality-enriched SWCNTs ([SWCNTs (6,5)] was reported [44].…”

Section: Polymer/swcnt Hybridsmentioning

confidence: 99%

Photoinduced electron transfer processes of single-wall carbon nanotube (SWCNT)–based hybrids

Xiong

Chan

et al. 2020

Nanophotonics

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In this review, noncovalent functionalization of single-wall carbon nanotubes (SWCNTs) is briefly reviewed. The functional materials summarized here include metalloporphyrin derivatives, biomolecules and conjugated polymers. Notably, time-resolved spectroscopic techniques such as time-resolved fluorescence and transient absorption were employed to directly investigate the electron transfer and recombination processes between the functionalities and the SWCNTs. In addition, Raman spectroscopy is also useful to identify the interaction and the electron transfer direction between both the functionalities and the SWCNTs. An improved understanding of the mechanisms of these SWCNT-based nanohybrids in terms of their structural and photophysical properties can provide more insights into the design of new electronic materials.

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Section: Polymer/swcnt Hybridsmentioning

confidence: 99%

Photoinduced electron transfer processes of single-wall carbon nanotube (SWCNT)–based hybrids

Xiong

Chan

et al. 2020

Nanophotonics

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“…[ 26 ] When functionalized with a variety of biocompatible tags, NDIs are versatile synthetic scaffolds and their potential applications are already extending to biomedical imaging fi elds. [27][28][29][30] These aromatic molecules have demonstrated their capability to across cellular membranes [ 31,32 ] and favor the up-take of carbon based materials such as Single Walled Carbon Nanotubes (SWNTs). [ 33 ] Such behavior seems to be independent from the primary amine employed for the synthesis of NDIs and rather be driven by the planar naphthalene diimide cores.…”

Section: Thermally Reduced Graphene Oxide Nanohybrids Of Chiral Functmentioning

confidence: 99%

“…[ 31 ] These optical properties combined with biocompatibility have rendered them ideal candidates for further functionalization and exploitation for fl uorescent bioimaging. [ 30,31,33 ] The assembly process between NDIs and nanomaterials such as C 60 , C 70 , and SWNTs has been explored, by us and others. [ 33,[35][36][37] Recently, an interest in understanding their interactions with planar carbon system (denoted here PCS) has emerged and these are believed to be based on noncovalent contacts such as π-stacking coupled with hydrophobic interactions and Coulombic attractions of the electron deficient NDI core to the electron rich surface of graphene and its derivatives.…”

Section: Thermally Reduced Graphene Oxide Nanohybrids Of Chiral Functmentioning

confidence: 99%

Thermally Reduced Graphene Oxide Nanohybrids of Chiral Functional Naphthalenediimides for Prostate Cancer Cells Bioimaging

Tyson

Mirabello

Calatayud

et al. 2016

Adv Funct Materials

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This study reports on the supramolecular assemblies formed between planar carbon systems (PCSs) such as thermally reduced graphene oxide (TRGO) and its small‐molecule model system coronene and a series of d‐ and l‐α amino acid derivatized naphthalenediimides (NDIs) where the halogen substituents (X = F, Cl, Br, I) are varied systematically. Confocal fluorescence microscopy of NDIs, NDI•coronene, and NDI•TRGO complexes is performed proving the uptake and stability of such complexes in the cellular environment and suggesting their potential as prostate cancer imaging agents. 1H NMR and UV–vis spectroscopy studies support the formation of charge transfer complexes whereby the increasing polarizability and general electronegativity of the aryl halide substituted at the NDI periphery influence the magnitude of the association constants in the ground state between NDI and coronene. Complexation between NDIs and PCSs also results in stable photoexcited assemblies within the solution (coronene) as well as the dispersed phased (TRGO). Fluorescence emission titrations and 2‐photon time correlated single photon counting measurements suggest the existence of dynamic quenching mechanisms upon the excitation of the fluorophore in the presence of the carbon substrates, as these methods are sensitive proves for the subtle changes in the NDI environment. The series of halogenated species used exerts supramolecular control over the degree of surface assembly on the TRGO and over the interactions with the coronene molecule, and this is of relevance to the assembly of future biosensing platforms as these materials can both be viewed as congeners of graphene. Finally, MTT assays carried out in PC‐3 cells demonstrate that the stable noncovalent functionalization of TRGO and coronene with either l or d NDIs remarkably improves the cellular viability in the presence of such graphene‐like materials. These phenomena are of particular relevance for the understanding of the direct donor–acceptor interactions in solutions which govern the design of nanomaterials with future biosensing and bioimaging applications.

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“…25,26 By comparing the NDI1@SWCNTs spectrum with the one of the two starting materials, the features of both components in the hybrid material are evident. Whereas no considerable shifts take place on the NDI1 features (Supplementary Material, Figure S5), 18 several changes are evident in the SWCNT part. In the near infrared region, the intensity of the features is relatively lower, while some of these bands have disappeared (Figure 2).…”

Section: Resultsmentioning

confidence: 96%

Selective Interaction of a Water Soluble Naphthalenediimide with Single-Walled Carbon Nanotubes

Syrgiannis

Rigodanza

Prato

2017

ECS J. Solid State Sci. Technol.

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Carbon Nanotubes (CNTs) are amongst the more used nanomaterials of the last decades. They have been applied to different fields, including electronics, solar cells, catalysis and nanomedicine.1,2 One of the main drawbacks for their use in most applications is the strong tendency to aggregate and the poor solubility in any solvent, organic or aqueous. Chemical functionalization is the best solution to make this material not only easier to manipulate and to handle, 3 but also more biocompatible. 4 However, covalent functionalization may modify the sp 2 character of the carbon framework and consequently can influence their properties. 5,6 Non-covalent approaches take advantage of supramolecular interactions, where the adsorption of organic and inorganic molecules on the surface of CNTs lead to stable suspensions. 7The possibility to recognize and sort selected types of CNTs is of prominent interest, since the electronic and optical properties strongly depend on their structural parameters (diameter and helicity). 8 As a consequence, a structural control of SWCNTs is required for their use, especially in electronic and optical applications. Although several methods for the selective synthesis of specific types of SWCNTs have been devised, there are still problems of size heterogeneity. Therefore, post growth separation approaches, such as density gradient ultracentrifugation, 9 electrophoresis, 10 chromatography 11 and molecule assisted selective extractions [12][13][14] are currently employed to minimize size dispersion. While the use of n-type semiconductors for selective adsorption on SWCNTs have been successfully reported, 15,16 here we discuss the non-covalent interaction of a water soluble naphthalenediimide derivative (NDI1) with SWCNTs. The naphthalenediimides are the smallest n-type semiconductor analogs in the family of rylenes.17 Their shape and rich π system makes them as good candidates for the formation of interesting hybrid materials with SWCNTs. Only a few articles employing NDIs as surfactants for CNTS have been reported. 18,19 In this work, we have used a bis-cationic NDI (Scheme 1), which can interact strongly with the scaffold of SWCNTs. This interaction appears to be selective to some types of SWCNTs, by adsorbing on the smaller diameter nanotubes. Methods NDI1with Iodide as counter anion was synthesized as reported previously. 20 The bis-chloride derivative was synthesized by following the procedure that is reported in the Supplementary Material. The hybrid with SWCNTs was prepared by using the following procedure: 3 mg of NDI1 were solubilized in 5 ml of milliQ H 2 O. 3 mg of HiPco SWCNTs (batch n. HP27-078) were dispersed in 5 ml milliQ H 2 O with the assistance of sonication (30 min). The two solutions were mixed and the resulting suspension was sonicated for further 30 min, followed by magnetic stirring (2 h). The final mixture was filtered and washed several times with H 2 O. The solid was redispersed in D 2 O and z E-mail: zsyrgiannis@units.it; prato@units.it Scheme 1. Structure of NDI1.c...

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Naphthalenebisimides as photofunctional surfactants for SWCNTs – towards water-soluble electron donor–acceptor hybrids

Abstract: A water soluble naphthalenebisimide derivative (NBI) was synthesized and probed to individualize, suspend, and stabilize single wall carbon nanotubes (SWCNT).

Cited by 13 publications

References 75 publications

Photoinduced electron transfer processes of single-wall carbon nanotube (SWCNT)–based hybrids

Photoinduced electron transfer processes of single-wall carbon nanotube (SWCNT)–based hybrids

Thermally Reduced Graphene Oxide Nanohybrids of Chiral Functional Naphthalenediimides for Prostate Cancer Cells Bioimaging

Selective Interaction of a Water Soluble Naphthalenediimide with Single-Walled Carbon Nanotubes

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