Tuning the Carbon Nanotube Selectivity: Optimizing Reduction Potentials and Distortion Angles in Perylenediimides

Published on Mar 19, 2018in Journal of the American Chemical Society15.419
· DOI :10.1021/JACS.8B00452
Peter W. Münich6
Estimated H-index: 6
(FAU: University of Erlangen-Nuremberg),
Christoph Schierl7
Estimated H-index: 7
(FAU: University of Erlangen-Nuremberg)
+ 7 AuthorsDirk M. Guldi111
Estimated H-index: 111
(FAU: University of Erlangen-Nuremberg)
Sources
Abstract
Different water-soluble perylenediimides (PDIs) have been used to individualize and stabilize single-walled carbon nanotubes (SWCNTs) in aqueous media. A key feature of the PDIs is that they can be substituted at the bay positions via the addition of two and/or four bromines. This enables control over structural and electronic PDI characteristics, which prompted us to conduct comparative assays with focus on SWCNTs’ chirality and charge transfer. Electrochemical, microscopic, and spectroscopic experiments were used to investigate the SWCNT chiral selectivity of PDIs, on the one hand, and charge-transfer reactions between SWCNTs and PDIs, on the other hand.
📖 Papers frequently viewed together
2010
201513.28Small
9 Authors (R. Thomas Weitz)
References68
Newest
#9Maurizio Prato (UniTS: University of Trieste)H-Index: 124
The aggregation and the photophysics of a water soluble perylenediimide (PDI) derivative that features two bromine substituents in the bay positions has been probed. Non-fluorescent aggregates were found to be present at concentrations of 1.0 × 10−5 M. In situ small-angle X-ray scattering (SAXS) measurements and complementary molecular modeling showed the presence of PDI aggregates. In their singlet excited states, the PDI aggregates are characterized by distinct transient fingerprints and rapid...
Source
#1Juho Lee (KAIST)H-Index: 10
#2Ji Il Choi (KAIST)H-Index: 14
Last. Yong-Hoon Kim (KAIST)H-Index: 30
view all 6 authors...
While one of the most promising applications of carbon nanotubes (CNTs) is to enhance polymer orientation and crystallization to achieve advanced carbon fibers, the successful realization of this goal has been hindered by the insufficient atomistic understanding of polymer-CNT interfaces. We herein theoretically study polyacrylonitrile (PAN)-CNT hybrid structures as a representative example of polymer-CNT composites. Based on density-functional theory calculations, we first find that the relativ...
Source
#1Kalaivanan Nagarajan (Indian Institute of Science Education and Research, Thiruvananthapuram)H-Index: 14
#2Ajith R. Mallia (Indian Institute of Science Education and Research, Thiruvananthapuram)H-Index: 11
Last. Mahesh Hariharan (Indian Institute of Science Education and Research, Thiruvananthapuram)H-Index: 24
view all 4 authors...
We describe the design, bottom-up synthesis and X-ray single crystal structure of systematically twisted aromatics 1c and 2d for efficient intersystem crossing. Steric congestion at the cove region creates a nonplanar geometry that induces a significant yield of triplet excited states in the electron-poor core-twisted aromatics 1c and 2d. A systematic increase in the number of twisted regions in 1c and 2d results in a concomitant enhancement in the rate and yield of intersystem crossing, monitor...
Source
Pure carbon nanotubes (CNT) and CNT–polymer composites have many useful properties, ranging from electrical conductivity to superior mechanical strength. However, the full potential of using CNTs as reinforcements (in a polymer matrix, for example) has been severely limited because of complications associated with the dispersion of CNTs. CNTs tend to entangle with each other, forming materials with properties that fall short of expectations. One of the effective ways of dispersing CNTs is the us...
Source
#1Volker Strauss (FAU: University of Erlangen-Nuremberg)H-Index: 24
#2Alexandra Roth (FAU: University of Erlangen-Nuremberg)H-Index: 9
Last. Dirk M. Guldi (FAU: University of Erlangen-Nuremberg)H-Index: 111
view all 4 authors...
Summary In this review, we survey the role of carbon-based nanomaterials in energy-conversion schemes. In particular, we highlight charge-transfer processes on the molecular scale in sp 2 carbon in zero dimensions (fullerenes), sp 2 carbon in one dimension (carbon nanotubes), sp 2 carbon in two dimensions (graphene), and sp 2 /sp 3 carbon in zero and two dimensions (defectuous carbon nanostructures). As such, we conclude that the versatility of carbon-based nanomaterials in terms of structural a...
Source
#1Tejas A. Shastry (NU: Northwestern University)H-Index: 14
#2Patrick E. Hartnett (NU: Northwestern University)H-Index: 14
Last. Mark C. Hersam (NU: Northwestern University)H-Index: 113
view all 5 authors...
Polymer solar cells (PSCs) have achieved power conversion efficiencies exceeding 10%, but their performance has been limited under concentrated sunlight because of poor stability and recombination processes despite their potential for low-cost concentrated solar power. Recently, ternary polymer solar cell blends have been explored as a strategy to improve PSC performance; however, this approach has been demonstrated only for polymer–fullerene solar cells with organic ternary additives and has no...
Source
#1Emiliano Martínez-Periñán (UAM: Autonomous University of Madrid)H-Index: 10
#2Alberto de Juan (IMDEA Nanoscience)H-Index: 10
Last. Emilio M. Pérez (IMDEA Nanoscience)H-Index: 33
view all 10 authors...
We describe the functionalization of SWNTs enriched in (6,5) chirality with electron donating macrocycles to yield rotaxane-type mechanically interlocked carbon nanotubes (MINTs). Investigations by means of electron microscopy and control experiments corroborated the interlocked nature of the MINTs. A comprehensive characterization of the MINTs through UV-vis-NIR, Raman, fluorescence, transient absorption spectroscopy, cyclic voltammetry, and chronoamperometry was carried out. Analyses of the sp...
Source
#1Marc Rudolf (International Council on Mining and Metals)H-Index: 11
#2S. V. Kirner (FAU: University of Erlangen-Nuremberg)H-Index: 1
Last. Dirk M. Guldi (LBNL: Lawrence Berkeley National Laboratory)H-Index: 111
view all 3 authors...
In this review article, we highlight recent advances in the field of solar energy conversion at a molecular level. We focus mainly on investigations regarding fullerenes as well as endohedral metallofullerenes in energy and/or electron donor–acceptor conjugates, hybrids, and arrays, but will also discuss several more advanced systems. Hereby, the mimicry of the fundamental processes occurring in natural photosynthesis, namely light harvesting (LH), energy transfer (EnT), reductive/oxidative elec...
Source
#1Konstantin Dirian (FAU: University of Erlangen-Nuremberg)H-Index: 8
#2Susanne Backes (FAU: University of Erlangen-Nuremberg)H-Index: 3
Last. Dirk M. Guldi (FAU: University of Erlangen-Nuremberg)H-Index: 111
view all 8 authors...
A water soluble naphthalenebisimide derivative (NBI) was synthesized and probed to individualize, suspend, and stabilize single wall carbon nanotubes (SWCNTs). Besides a comprehensive photophysical and electrochemical characterization of NBI, stable suspensions of SWCNTs were realized in buffered D2O. Overall, the dispersion efficiency of the NBI surfactant was determined by comparison with naphthalene based references. Successful individualization of SWCNTs was corroborated in several microscop...
Source
#1Volker Strauss (FAU: University of Erlangen-Nuremberg)H-Index: 24
#2Johannes T. Margraf (FAU: University of Erlangen-Nuremberg)H-Index: 24
Last. Dirk M. Guldi (FAU: University of Erlangen-Nuremberg)H-Index: 111
view all 4 authors...
The thrust of this work is to integrate small and uniformly sized carbon nanodots (CNDs) with single-walled carbon nanotubes (SWCNT) of different diameters as electron donors and electron acceptors, respectively, and to test their synergetic interactions in terms of optoelectronic devices. CNDs (denoted pCNDs, where p indicates pressure) were prepared by pressure-controlled microwave decomposition of citric acid and urea. pCNDs were immobilized on single-walled carbon nanotubes by wrapping the l...
Source
Cited By11
Newest
#1Ilias Papadopoulos (FAU: University of Erlangen-Nuremberg)H-Index: 8
#2Arjun Menon (FAU: University of Erlangen-Nuremberg)H-Index: 4
Last. Dirk M. Guldi (FAU: University of Erlangen-Nuremberg)H-Index: 111
view all 9 authors...
In this contribution, the excited state charge-transfer interactions between single-walled carbon nanotubes (SWCNTs) and a variety of phenyl, 4-bromophenyl, and thiophene substituted diketopyrrolopyrroles (DPPs), is described. Atomic force microscopy (AFM) and aberration corrected high resolution transmission electron microscopy (AC-HRTEM) corroborated the successful formation of DPP/SWCNTs. Steady-state absorption, fluorescence, and Raman spectroscopies all gave insights into the impact on thei...
Source
#1Anasheh Maridiroosi (TMU: Tarbiat Modares University)H-Index: 1
#2Abdolghafar Abolhosseini Shahrnoy (TMU: Tarbiat Modares University)H-Index: 7
Last. Peyman Afsar (TMU: Tarbiat Modares University)H-Index: 1
view all 4 authors...
Abstract Herein an effective and facile approach for introducing photoactive and stable hybrid of graphene oxide (GO) and perylenediimide (PDI) was presented. For this purpose, we have synthesized amidated GO and then by reaction between amidated GO and asymmetric PDI, hybrid (GNP) was produced. The studies on the stability and on the dispersibility of this hybrid showed that the GNP hybrid is stable and dispersible in aqueous solution. This hybrid considered as a sensitizer for photocatalytic p...
Source
#1Ritabrata Sarkar (University of Gour Banga)H-Index: 10
#2Moumita Kar (Visva-Bharati University)H-Index: 9
Last. Oleg V. Prezhdo (SC: University of Southern California)H-Index: 86
view all 8 authors...
Carbon nanotubes (CNTs) are appealing candidates for solar and optoelectronic applications. Traditionally used as electron sinks, CNTs can also perform as electron donors, as exemplified by coupling with perylenediimide (PDI). To achieve high efficiencies, electron transfer (ET) should be fast, while subsequent charge recombination should be slow. Typically, defects are considered detrimental to material performance because they accelerate charge and energy losses. We demonstrate that, surprisin...
Source
#1Arjun Menon (FAU: University of Erlangen-Nuremberg)H-Index: 4
#2Peter W. Münich (FAU: University of Erlangen-Nuremberg)H-Index: 6
Last. Dirk M. Guldi (FAU: University of Erlangen-Nuremberg)H-Index: 111
view all 5 authors...
Herein, the microscopic and spectroscopic characterization of a novel non-covalent electron donor-acceptor system, in which three different metalloporphyrins (1, 2, and 3) play the dual role of light harvester and electron donor with SWCNTs as electron acceptor, is described. To this end, microscopy, that is, atomic force microscopy (AFM) and transmission electron microscopy (TEM) corroborate the formation of 1-SWCNT, 2-SWCNT, and 3-SWCNT. Spectroscopy by means of Raman, fluorescence, and transi...
Source
#1Ritabrata Sarkar (University of Gour Banga)H-Index: 10
#2Habib (University of Gour Banga)H-Index: 5
Last. Oleg V. Prezhdo (SC: University of Southern California)H-Index: 86
view all 4 authors...
Supramolecular nanohybrids composed of carbon nanotubes (CNTs) and organic molecules are appealing candidates for many applications. We investigate charge separation and recombination dynamics in extended tetrathiafulvalene (exTTF), a well-known sulfur (S)-rich electron donor, immobilized on a CNT surface, and study the role of the chalcogen atom by comparing with the selenium (Se)-rich tetraselenafulvalene (exTSeF) analog. Using real-time time-dependent tight-binding density-functional theory c...
Source
#1Olga A. Stasyuk (University of Girona)H-Index: 13
#2Anton J. Stasyuk (University of Girona)H-Index: 12
Last. Miquel SolàH-Index: 73
view all 4 authors...
Functionalization of nanotubes with donor and acceptor partners by the Bingel reaction leads to formation of charge-transfer dyads, which can operate in organic photovoltaic devices. In this work, ...
Source
Source
#1Marina Garrido (Complutense University of Madrid)H-Index: 4
#2Michel Volland (FAU: University of Erlangen-Nuremberg)H-Index: 7
Last. Dirk M. Guldi (FAU: University of Erlangen-Nuremberg)H-Index: 111
view all 9 authors...
A series of molecular precursors, containing one (1 and 3) or three pyrene (2 and 4) anchors, covalently linked to porphyrins (free base or Zn), were prepared and characterized. All of them enable their π-π stacking onto low-dimensional nanocarbons including single-walled carbon nanotubes (SWCNTs) and nanographene (NG), their individualization, and their characterization. Microscopic (TEM, AFM) and spectroscopic (steady state UV−Vis and fluorescence, spectroelectrochemistry, and transient absorp...
Source
#1Timothy A. Barendt (University of Oxford)H-Index: 7
#2William K. Myers (University of Oxford)H-Index: 23
Last. Paul D. Beer (University of Oxford)H-Index: 92
view all 8 authors...
The powerful electron accepting ability of fullerenes makes them ubiquitous components in biomimetic donor-acceptor systems that model the intermolecular electron transfer processes of Nature’s photosynthetic centre. Exploiting perylene diimides (PDIs) as components in cyclic host systems for the non-covalent recognition of fullerenes is unprecedented, in part because archetypal PDIs are also electron deficient, making dyad assembly formation electronically unfavourable. To address this, we repo...
Source
Last. Francis D'Souza (UNT: University of North Texas)H-Index: 76
view all 9 authors...
A novel zinc phthalocyanine–benzoperylenetriimide conjugate has been synthesized and its ability to undergo ultrafast energy and electron transfer as a function of solvent polarity has been demonstrated using the femtosecond transient absorption (fs-TA) technique operating at a femto- to nanosecond time scale.
Source
This website uses cookies.
We use cookies to improve your online experience. By continuing to use our website we assume you agree to the placement of these cookies.
To learn more, you can find in our Privacy Policy.