Stable Electron Donor–Acceptor Nanohybrids by Interfacing n‐Type TCAQ with p‐Type Single‐Walled Carbon Nanotubes

Abstract

Getunte Kohlenstoffröhren: Eine elektronenakzeptierende Nanopinzette aus 11,11,12,12‐Tetracyano‐9,10‐anthrachinodimethan (TCAQ), die mit Carbonsäure enthaltenden dendritischen Einheiten funktionalisiert ist, bildet mit einwandigen Kohlenstoffnanoröhren (SWCNTs) außergewöhnlich stabile wässrige n‐/p‐Dispersionen. Nach Lichtanregung gehen die Nanohybride einen weniger bekannten Elektronentransfer von der SWCNT zur TCAQ‐Nanopinzette ein.

Efficient Energy-Conversion Materials for the Future: Understanding and Tailoring Charge-Transfer Processes in Carbon Nanostructures

“…Evidence of a reductive charge transfer from SWCNTs came from Raman assays, in which an upshift of the 2D mode of 7 cm À1 was noted, and from unambiguous differential absorption characteristics of the one-electron reduced ZnPc detected in pumpprobe measurements. Extraordinary strong interactions with n-type semiconductors have also been reported for TCAQ 54 and PDI. 55,56 By means of exploiting p-stacking and chargetransfer interactions with especially PDI, a number of efficient electroactive surfactants that secured the stabilization of individualized SWCNTs in aqueous solutions were developed.…”

Chemistry in Stereo: The 49th Bürgenstock Conference

“…[13] The final day commenced with the talk by Jesus JimØnez-Barbero (CSCI, Madrid) on molecular recognition studied by saturation transfer difference (STD) NMR spectroscopy. The evening lecture by Nazario Martín (Universidad Complutense de Madrid) took us into the world of nanocarbons.…”

“…His talk included impressions of supramolecular interactions of p-extended tetrathiafulvalenes(exTTF)modified carbon nanoforms and their application as electrically conducting materials. [13] The final day commenced with the talk by Jesus JimØnez-Barbero (CSCI, Madrid) on molecular recognition studied by saturation transfer difference (STD) NMR spectroscopy. [14] He presented the latest on glycan receptor interactions as well as the interplay of cytotoxic small molecules, such as epothilone, with tubulins.…”

Modified SWCNTs with Amphoteric Redox and Solubilizing Properties

“…[4] We have recently ex-plored the p-doping of SWCNTs with the n-type electron-acceptor unit TCAQ by considering a supramolecular approach and demonstrated that this electroactive unit effectively individualizes SWCNTs when combined with a dendronized core. [16] The TCAQ family provides suitable electron-acceptor systems that have been investigated as strong electron acceptors in charge-transfer complexes, at metal interfaces, and covalently connected to conjugated polymers and fullerenes. [17] TCAQs exhibit low reduction potential values and their central para-quinoid moiety confers high stability to the aromatic reduced species.…”

“…Although various n ‐type electron acceptors have been bound to SWCNTs by using noncovalent interactions,15 the covalent approach has been scarcely investigated with respect to the electron‐donating ability of SWCNTs 4. We have recently explored the p ‐doping of SWCNTs with the n ‐type electron‐acceptor unit TCAQ by considering a supramolecular approach and demonstrated that this electroactive unit effectively individualizes SWCNTs when combined with a dendronized core 16. The TCAQ family provides suitable electron‐acceptor systems that have been investigated as strong electron acceptors in charge‐transfer complexes, at metal interfaces, and covalently connected to conjugated polymers and fullerenes 17.…”