Alternative Donor−Acceptor Stacks from Crown Ethers and Naphthalene Diimide Derivatives: Rapid, Selective Formation from Solution and Solid State Grinding

Koshkakaryan, Gayane; Klivansky, Liana M.; Cao, Dennis; Šnauko, Marián; Teat, Simon J.; Struppe, Jochem; Liu, Yi

doi:10.1021/ja809088v

Cited by 101 publications

(50 citation statements)

References 32 publications

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“…[ 18 ] All compounds ND1 − ND4 were obtained with yields of 79%−97%. The compounds ND1 , [ 19 ] ND2 , and ND3 [ 20 ] are prepared as model compounds for the direct comparison of the properties with other molecules of the series.…”

Section: Synthesismentioning

confidence: 99%

New Electron Transport Materials for High Performance Organic Solar Cells: Synthesis and Properties of Symmetrical and Asymmetrical 1,4,5,8‐Naphthalenetetracarboxylic Dianhydride Derivatives

Kukhta

Zeika

Widmer

et al. 2016

Adv Elect Materials

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Two series – symmetrical and asymmetrical – of electron‐transporting 1,4,5,8‐naphthalenetetracarboxylic dianhydride derivatives are designed and synthesized. The compounds show high thermal stability with initial destruction temperatures reaching 481 °C. The materials absorb light in UV–visible region, however, avoiding parasitic absorption that makes them suitable for the usage in high performance solar cells. Cyclic voltammetry deduces relatively high electron affinity (3.84–4.10 eV) indicating strong electron accepting nature of the molecules. The synthesized compounds have remarkable electrical properties such as high conductivity (up to 4 × 10−5 S cm−1) and electron mobility (up to 10−3 cm2 V−1 s−1). The highest solar cell efficiency is obtained for asymmetrical adduct of 1,4,5,8‐naphthalenetetracarboxylic dianhydride, pyridine‐3‐amine, and pyridin‐3,4‐diamine, and exceeds the efficiency of the reference material C60. A comparative study of the experimentally estimated and theoretically calculated by means of density functional theory method characteristics of the electron‐transporting materials is presented. The control of the symmetry of the molecular structures is responsible for the high performance of compounds in the target devices.

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Section: Synthesismentioning

confidence: 99%

New Electron Transport Materials for High Performance Organic Solar Cells: Synthesis and Properties of Symmetrical and Asymmetrical 1,4,5,8‐Naphthalenetetracarboxylic Dianhydride Derivatives

Kukhta

Zeika

Widmer

et al. 2016

Adv Elect Materials

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“…Solid-state grinding 5 is a very important procedure for preparing Maya Blue and other functional materials by promoting the interactions between guest and host species. 30,31 The mixture of white LRD and rose-red PR 31 became a homogeneous rose-red powder after ground for a few minutes. Such a color change implies interaction between 10 LRD and PR 31.…”

Section: Preparation Of Lrd/pr 31mentioning

confidence: 99%

Water-dispersible and stable fluorescent Maya Blue-like pigments

et al. 2015

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Poor water-dispersibility and stability of hydrophobic fluorescent organic pigments (HFOPs) hinder many 5 of their applications. Inspired by the excellent stability of Maya Blue pigments and the water solubility of Laponite RD (LRD), we report facile synthesis of water-dispersible and stable fluorescent Maya Blue-like pigments via the host-guest interaction between LRD and Pigment Red 31 (PR 31), a representative HFOP. The concentration of LRD and solid-state grinding play important roles in effectively dispersing PR 31 into the aqueous solution. The interactions between PR 31 and LRD involve van der Waals, π-π, 10 electrostatic, hydrogen bonding between phenolic hydroxyl groups of PR 31 and silanols of LRD as well as dye-dye hydrophobic interactions. The interactions between PR 31 and LRD occur on the external surface of LRD and the entrance of the micropores of LRD, however, the PR 31 molecules cannot intercalate into the layers of LRD plates. The so-obtained pigments are highly water-dispersible, and very stable to thermal aging and UV irradiation owing to the interactions between LRD and PR 31, and the 15 shielding effect of LRD.

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“…40 Charge transfer complexes containing columnar alternating ADA stacks could be readily tuned to modulate electronic, optical, and ferroelectric properties. These complexes were usually obtained in solution through solvophobic or ion-binding interactions.…”

Section: Control Of Chemical Events Including Self-healing and Molecumentioning

confidence: 99%

Control of nano/molecular systems by application of macroscopic mechanical stimuli

2011

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The potential usefulness and importance of nanomaterials are now well recognized. However, currently available synthetic nanomaterials are generally used in their bulk form and control of nanosystems at the nanoscale on demand has not been realized. To solve this problem, the use of macroscopic mechanical stimuli to drive nano/molecular systems is considered to be a key technique. If direct manipulation of nano/molecular systems could be achieved by applying macroscopic mechanical stimuli, we might exert control over nanotechnological systems according to our needs. In this perspective, recent methodologies for controlling nano/molecular systems through application of macroscopic mechanical forces are introduced. Application of mechanical processes is known to affect some molecular association and chemical reactions, causing variation of optical properties, sometimes resulting in self-healing functions or capture and release of molecules under macroscopic mechanical motions. We might be able to realize the great potential of nanoscale and molecular systems by accessing nanoscience and nanotechnology from the macroscopic world.Accessing nano from macro: learning from Nature 'Nanoscience' and 'nanotechnology' were formerly technical terms in specialized research areas but they have recently entered everyday use, and the importance of nanomaterials is now well recognized. 1-18 However, currently available synthetic nanomaterials are generally used in their bulk form (e.g., as polymer fillers), and control of nanosystems at the nanoscale on demand has not been realized. Thus, nanotechnology might be seen as an immature technology partly because of the lack of means for connecting the nanoscopic world with our activities in the macroscopic world. Integration of the nanoscopic and macroscopic worlds is one of the anticipated breakthroughs for nanotechnology and may bring great benefits to society.Approaches for accessing nano from macro require a means to connect bulk stimuli with molecular level systems. Electronic and photonic stimuli can be respectively regarded as pulses of electrons and photons, which can interact with nano/molecular systems. Similarly, chemical stimuli can be divided at the molecular level into single molecule events. There exist a variety of molecular machines, including motors and tweezers, which have been demonstrated to operate under such stimuli. [19][20][21] In those systems, intramolecular rotations and/or deformations can be stimulated by applying photonic or chemical inputs. In contrast, it is currently challenging to drive nano/molecular systems by applying macroscopic mechanical stimuli since we cannot directly manipulate molecules. However, driving

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Alternative Donor−Acceptor Stacks from Crown Ethers and Naphthalene Diimide Derivatives: Rapid, Selective Formation from Solution and Solid State Grinding

Cited by 101 publications

References 32 publications

New Electron Transport Materials for High Performance Organic Solar Cells: Synthesis and Properties of Symmetrical and Asymmetrical 1,4,5,8‐Naphthalenetetracarboxylic Dianhydride Derivatives

New Electron Transport Materials for High Performance Organic Solar Cells: Synthesis and Properties of Symmetrical and Asymmetrical 1,4,5,8‐Naphthalenetetracarboxylic Dianhydride Derivatives

Water-dispersible and stable fluorescent Maya Blue-like pigments

Control of nano/molecular systems by application of macroscopic mechanical stimuli

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