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Core-substituted naphthalenediimides

Naomi Sakai, +3 more
- 07 Jun 2010 - 
- Vol. 46, Iss: 24, pp 4225-4237
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TLDR
Research of core-substituted naphthalenediimides (cNDIs) is reviewed in a comprehensive yet easily readable manner with emphasis on the ability of cNDIs with electron donating substituents to absorb and fluoresce in all colors without global structural changes.
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This article is published in Chemical Communications.The article was published on 2010-06-07 and is currently open access. It has received 461 citations till now.

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Journal ArticleDOI

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

TL;DR: This comprehensive review surveys developments over the past decade in the field of naphthalene diimides and explores their application toward: supramolecular chemistry; sensors; host-guest complexes for molecular switching devices; ion-channels by ligand gating; gelators for sensing aromatic systems; catalysis through anion-π interactions; and NDI intercalations with DNA for medicinal applications.
Journal ArticleDOI

Putting anion-π interactions into perspective.

TL;DR: The objectives of this Review are to discuss current thinking on the nature of this interaction, to survey key experimental work in which anions-π bonding is demonstrated, and to provide insights into the directional nature of anion-π contact in X-ray crystal structures.
Journal ArticleDOI

The Bright Future of Unconventional σ/π-Hole Interactions

TL;DR: The physical nature of σ- and π-hole interactions is described, a selection of inquiries that utilise ρ- andπ-holes are presented, and an overview of analyses of structural databases (CSD/PDB) that demonstrate how prevalent these interactions already are in solid-state structures are given.
References
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Conjugated polymer-based organic solar cells

TL;DR: This review gives a general introduction to the materials, production techniques, working principles, critical parameters, and stability of the organic solar cells, and discusses the alternative approaches such as polymer/polymer solar cells and organic/inorganic hybrid solar cells.
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Polymer–Fullerene Composite Solar Cells

TL;DR: Polymer-based organic photovoltaic systems hold the promise for a cost-effective, lightweight solar energy conversion platform, which could benefit from simple solution processing of the active layer.
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A high-mobility electron-transporting polymer for printed transistors

TL;DR: A highly soluble and printable n-channel polymer exhibiting unprecedented OTFT characteristics under ambient conditions in combination with Au contacts and various polymeric dielectrics is reported and all-printed polymeric complementary inverters have been demonstrated.
Journal ArticleDOI

Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures

TL;DR: Perylene bisimide dyes and their organization into supramolecular architectures through hydrogen-bonding, metal ion coordination and pi-pi-stacking is discussed; further self-assembly leading to nano- and meso-scopic structures and liquid-crystalline compounds is also addressed.
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Q1. What are the contributions in this paper?

This feature article reviews research of core-substituted napthalenediimides ( cNDIs ) in a comprehensive yet easy readable manner. 

The intercalation of dialkoxyanthracene 101 has been used to sense polyphenols such as epigallocatechin gallate 102 within synthetic pores with internal NDI tweezers. 

Rainbow cNDIs have been coupled with zinc chlorins to harvest light at the periphery of zinc chlorin rod antennas and transfer the photonic energy to the chlorophyll centers. 

The successful fabrication of organic solar cells with cNDIEDOT polymers 80 is the first example where the ability of - stacked cNDIs to transport electrons is combined with light. 

The red cNDIs placed on top of the yellow cNDIs create a redox gradient in the e-channel that directs the electrons toward the gold surface. 

As with chlorophyll, the symmetry-breaking photoinduced charge separation with blue cNDIs 17 is 290 attractive for optoelectronics applications because it occurs with minimal losses in photonic energy. 

Electrostatic potential surfaces (blue positive, red negative) and computed axial quadrupole moments QZZ of cNDIs 83-86, adapted from refs. 

The introduction of the two alkoxy donors in the core of yellow cNDIs 13 raises the LUMO to -3.82 eV, and the first oxidation accounting for the HOMO level of -6.16 eV can be 185 determined directly by CV (Figures 2b and 1). 

Considering that 500 anionic reactive intermediates such as enolates should be similarly recognized on asymmetric -acidic surfaces, the impact of anion- interactions on organocatalysis is expected to be significant.7anionNNOOOOCNNCNNOOOONNOOOOCNNCNNOOOO105103 106104-acidity decrowdinganion binding anion transport505Fig. 10 Structure of NDIs and cNDIs 103-106 used to demonstrate the functional relevance of anion- interactions with regard to anion binding and transport across lipid bilayer membranes. 

With nanomolar effective concentrations, the transport activity of the ideal cNDI 106 is significant, as is the found selectivity toward size and nature of the transported anion. 

Addition of head-to-head dodecyl tails to the bithiophene donor increased bandgap and lowered the HOMO level of polymer 77, whereas the LUMO was not affected (Table 1, entry 50). 

605The replacement of the central thiophene in cNDI-OT polymers 81 with a fluorene in the fluorescent cNDI-OT polymers 82 has relatively little effect on the narrow bandgap ( max = 613 nm), indicating that strong electronic interactions 610 along the polymer chain are preserved (Table 1, entries 54- 55).36 

In monomeric POP-cNDI systems, the blue chromophores can undergo symmetry-breaking ultrafast and quantitative photoinduced charge separation with 685 a lifetime of 61 ps (Figure 3c). 

The transesterification that naturally occurs under these conditions is irrelevant because the obtained tetraester 36 is hydrolyzed anyway before the formation of yellow cNDIs 13 with the amines of choice. 

These 195 unique redox properties make cNDIs 17 similar to chlorophyll and very attractive for optoelectronic applications (see below).