Molecular Assemblies of Perylene Bisimide Dyes in Water

Görl, Daniel; Zhang, Xin; Würthner, Frank

doi:10.1002/anie.201108690

Cited by 441 publications

(290 citation statements)

References 181 publications

(150 reference statements)

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“…This type of evolution in our constructs' UV−vis spectra was indicative of strong pi−pi stacking interactions between the adjacent PTCDIs. [2][3][4][5][6][7][8]36 With our model constructs in hand, we proceeded to perform constant temperature molecular dynamics simulations for the PTCDI subunits of Oligo2 and Oligo3 (Figure 3). For simplicity, we only considered the structures shown in Figure 3 (denoted as P1, P2, and P3), removing the alkyl tails on the PTCDIs, the 3′ alkanethiol functionalities, the 5′ polyadenine tracts, and the terminal phosphate groups (when appropriate).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Molecular Dynamics Simulations of Perylenediimide DNA Base Surrogates

et al. 2015

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Perylene-3,4,9,10-tetracarboxylic diimides (PTCDIs) are a well-known class of organic materials. Recently, these molecules have been incorporated within DNA as base surrogates, finding ready applications as probes of DNA structure and function. However, the assembly dynamics and kinetics of PTCDI DNA base surrogates have received little attention to date. Herein, we employ constant temperature molecular dynamics simulations to gain an improved understanding of the assembly of PTCDI dimers and trimers. We also use replica-exchange molecular dynamics simulations to elucidate the energetic landscape dictating the formation of stacked PTCDI structures. Our studies provide insight into the equilibrium configurations of multimeric PTCDIs and hold implications for the construction of DNA-inspired systems from perylene-derived organic semiconductor building blocks.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Molecular Dynamics Simulations of Perylenediimide DNA Base Surrogates

et al. 2015

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“…[251] These covalent multichromophore ensembles will, however, not be discussed here as we put our focus on self-assembled H-and J-aggregates of PBIs as illustrative examples for dye-aggregate-based exciton transport systems. Towards such aggregate systems PBIs bear another advantage: These dyes are among the most strongly aggregating dye molecules known, showing sufficiently high binding constants not only in water [252] (where solvophobic effects prevail), but also in aliphatic and even in aromatic solvents. [253] Already in 2001, Würthner et al reported on the selfassembly of columnar aggregates of PBIs in methylcyclohexane (MCH).…”

Section: Supramolecular Systems: Perylene Bisimide H-and J-aggregatesmentioning

confidence: 99%

Exciton Transport in Molecular Aggregates – From Natural Antennas to Synthetic Chromophore Systems

Brixner

Hildner

Köhler

et al. 2017

Advanced Energy Materials

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The transport of excitation energy in molecular aggregates is of crucial importance for the function of organic optoelectronic devices and next‐generation solar cells. First, this review summarizes the theoretical background of the nature of the electronically excited states of molecular aggregates. For these systems, the electronic interaction between the monomers leads to the formation of exciton states. This goes along with a shift of the excitation energies and a redistribution of the oscillator strength with respect to the monomers. Next, a brief overview is provided over experimental techniques that allow to study the properties of excitons in molecular aggregates. This includes single‐molecule spectroscopy, coherent two‐dimensional (2D) spectroscopy, and single‐molecule coherent spectroscopy. Finally, examples of molecular aggregates spanning the range from natural systems that act in photosynthesis as light‐harvesting antennas to artificial aggregates built from synthetic chromophores are illustrated.

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“…[ 4 ] Hydrogen-bonding as a supramolecular engineering tool is useful to control self-assembly and highly relevant to aqueous and biochemical systems. [ 5,6 ] Recently, we have found that indigo, [ 7 ] and some of its derivatives [ 8,9 ] demonstrate ambipolar transport in organic fi eldeffect transistors (OFETs), with mobility ranging from 0.01-0.4 cm 2 V -1 s -1 . We…”

mentioning

confidence: 99%

Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes

Głowacki

Romanazzi

Yumusak

et al. 2014

Adv Funct Materials

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1wileyonlinelibrary.com IntroductionHydrogen-bonded organic pigments are a class of materials familiar from applications in the colorant industry, where they fi nd widespread use as materials for robust outdoor paints, cosmetics, and printing inks. [ 1,2 ] Indigo, a natural product, is the oldest and still most widely produced organic dye and pigment ( Figure 1 ). [ 3 ] The intermolecular -NH … O = hydrogen bonding that characterizes indigo is exploited in most of the synthetic hydrogen-bonded pigments as well. This class of materials has proven to be nontoxic and safe for humans, and is considered safer than even several classes of food dyes. [ 4 ] Hydrogen-bonding as a supramolecular engineering tool is useful to control self-assembly and highly relevant to aqueous and biochemical systems. [ 5,6 ] Recently, we have found that indigo, [ 7 ] and some of its derivatives [ 8,9 ] demonstrate ambipolar transport in organic fi eldeffect transistors (OFETs), with mobility ranging from 0.01-0.4 cm 2 V -1 s -1 . We Epindolidiones-Versatile and Stable Hydrogen-Bonded Pigments for Organic Field-Effect Transistors and Light-Emitting DiodesEric Daniel Głowacki , * Giuseppe Romanazzi , Cigdem Yumusak , Halime Coskun , Uwe Monkowius , Gundula Voss , Max Burian , Rainer T. Lechner , Nicola Demitri , Günther J. Redhammer , Nevsal Sünger , Gian Paolo Suranna and Serdar Sariciftci Hydrogen-bonded pigments are remarkably stable high-crystal lattice energy organic solids. Here a lesser-known family of compounds, the epindolidiones, which demonstrates electronic transport with extraordinary stability, even in highly demanding aqueous environments, is reported. Hole mobilities in the range 0.05-1 cm 2 V -1 s -1 can be achieved, with lower electron mobilities of up to 0.1 cm 2 V -1 s -1 . To help understand charge transport in epindolidiones, X-ray diffraction is used to solve the crystal structure of 2,8-difl uoroepindolidione and 2,8-dichloroepindolidione. Both derivatives crystallize with a linear-chain H-bonding lattice featuring two-dimensional π-π stacking. Powder diffraction indicates that the unsubstituted epindolidione has very similar crystallinity. All types of epindolidiones measured here display strong low-energy optical emission originating from excimeric states, which coexists with higher-energy fl uorescence. This can be exploited in light-emitting diodes, which show the same hybrid singlet and low-energy excimer electroluminescence. Low-voltage FETs are fabricated with epindolidione, which operate reliably under repeated cyclic tests in different ionic solutions within the pH range 3-10 without degradation. Finally, in order to overcome the insolubility of epindolidiones in organic solvents, a chemical procedure is devised to allow solution-processing via the introduction of suitable thermolabile solubilizing groups. This work shows the versatile potential of epindolidione pigments for electronics applications.

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Molecular Assemblies of Perylene Bisimide Dyes in Water

Cited by 441 publications

References 181 publications

Molecular Dynamics Simulations of Perylenediimide DNA Base Surrogates

Molecular Dynamics Simulations of Perylenediimide DNA Base Surrogates

Exciton Transport in Molecular Aggregates – From Natural Antennas to Synthetic Chromophore Systems

Epindolidiones—Versatile and Stable Hydrogen‐Bonded Pigments for Organic Field‐Effect Transistors and Light‐Emitting Diodes

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