Self-assembled naphthalenediimide derivative films for light-assisted electrochemical reduction of oxygen

Castaldelli, Evandro; Triboni, Eduardo Rezende; Demets, Grégoire Jean-François

doi:10.1039/c1cc10139k

Cited by 16 publications

(19 citation statements)

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“…These grains become more evident in the phase contrast image ( Figure 4D) with clear crystallized regions most likely of well aligned stacks of DC18. [27] This order …”

Section: Resultsmentioning

confidence: 99%

“…We have reported on the synthesis and electroactivity of the DC18 molecule previously. [27] DC18 is expected to be an excellent electron injection layer due to its inherent properties, being a charged cationic species with the high electron transport known to NDIs. From cyclic voltammetry measurements (Supplementary Info), the LUMO value for DC18 was calculated [28] to be -4.2eV, with the HOMO calculated using the optical bandgap to be -7.5eV.…”

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confidence: 99%

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Solution processed naphthalene diimide derivative as electron transport layers for enhanced brightness and efficient polymer light emitting diodes

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Increasing the efficiency and lifetime of polymer light emitting diodes (PLEDs) requires a balanced injection and flow of charges through the device, driving demand for cheap and effective electron transport/ hole blocking layers. Some materials, such as conjugated polyelectrolytes, have been identified as potential candidates but the production of these materials requires complex, and hence costly, synthesis routes. We have utilized a soluble small molecule naphthalene diimide derivative (DC18) as a novel electron transport/hole blocking layer in common PLED architectures, and compared its electronic properties to those of the electron transport/hole blocking small molecule bathocuproine (BCP). PLEDs incorporating DC18 as the electron transport layer reduce turn on voltage by 25%; increase brightness over three and a half times; and provide a full five-fold enhancement in efficiencies compared to reference devices. While DC18 has similar properties to the effective conjugated polyelectrolytes used as electron transport layers, it is simpler to synthesise, reducing cost while retaining favourable electron transport properties, and improves upon their degree for efficiency enhancement. The impact on device lifetime is hypothosized to be significant as well, due to the air-stability seen in many naphthalene diimide derivatives.

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“…These grains become more evident in the phase contrast image ( Figure 4D) with clear crystallized regions most likely of well aligned stacks of DC18. [27] This order …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solution processed naphthalene diimide derivative as electron transport layers for enhanced brightness and efficient polymer light emitting diodes

et al. 2013

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“…A base desta nova maneira de enxergar a química, segundo Toma, 2 está no "simples fato de acoplarmos várias unidades para gerar novas espécies com propriedades totalmente diferentes, visando obter alguma coisa mais inteligente, mais organizada; propõe a partir de moléculas isoladas, gerar uma estrutura ou arquitetura funcional". Sistemas supramoleculares têm sido desenvolvidos nas diferentes áreas possibilitando um grande conjunto de materiais diferenciados: lmes, 3 membranas, 4,5 micelas, 6,7 nanotubos, 8 cápsulas, 9 rotaxanos, 1012 máquinas moleculares, 13,14 etc. A criação de novos materiais tem implementado grandes áreas como as de catálise e energia.…”

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“…Outros modos vibracionais importantes identicados são 1595 cm −1 do estiramento dos carbonos da piridina, 1348 cm −1 e 1250 cm −1 dos estiramentos do C-H do naftaleno, e os estiramentos da estrutura C-N-C em 1192 cm −1 e 1118 cm −1 . 3,38,42,46,99,111,168,169 Os dados de FTIR são mais usados neste caso para observar as variações dos modos vibracionais da carbonila dos precursores ou subprodutos, como pode ser observado na gura 3. 10.…”

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Estudo das propriedades eletrônicas e espectroscópicas de uma série de diimidas naftálicas com substituintes aromáticos com potencial aplicação em dispositivos de armazenamento e conversão de energia

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“…DC4 não apresenta nenhum tipo de agregação no estado fundamental. A ausência de agregação da DC4 é esperada já que a mesma possui 2 cargas positivas ligadas no substituinte do anel imídico, que exercem repulsão eletrostática entre si evitando agregação.Entretanto, dados da literatura mostram a auto-agregação, através de fortes interações eletrônicas, de uma diimida funcionalizada no nitrogênio com 18 carbonos na cadeia alifática[Castaldelli et al 2011]. Os valores de absortividade molar (ε 381 27.613 M -1 .cm -1 e ε 360 22.016 M -1 .cm -1 ) são característicos de transição π,π*.…”

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Novos materiais funcionais organo-híbridos baseados em óxidos metálicos e diimidas aromáticas

Chagas-Silva¹

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As Naftaleno Diimidas interagiram de forma especial com nanopartículas de óxido de cério conferindo ausência de atividade hidrolítica e um comportamento X fotocrômico singular. Propõe-se que o corante orgânico se adsorve nas ranhuras das nanopartículas e, além disso forma dímeros estáveis que têm importância para as novas fotoatividades observadas. Palavras-chave:naftaleno diimidas, óxido de cério, material híbrido, agregados, fluorescência e surfactantes. XI Abstract (Chagas-Silva, F.A.C.) New Hybrid Functional Materials based in Metal Oxides and Aromatic Diimides. 2012. (150p). PhD Thesis -Graduate Program in Chemistry. Instituto de Química, Universidade de São Paulo, São Paulo.The use and study of hybrid materials is a challenge for the chemist to develop materials having new and superior qualities for applications in photonics, sensors and related areas. In this context one has to speculate on the properties of the organic and inorganic partners to achieve better and new properties.In this study the metal oxides (in particular Cerium Oxides), a special class among inorganic nanoparticles were selected to exploit their applications with an also special class of organic compounds the Naphthalene Diimides.Cerium Oxide is a wide bandgap semiconductor well known for its catalytic capabilities and for its simple manipulation to prepare thin films and nanoparticles. Naphthalene Diimides derivatives are known for their superior electrochemical activities comparable to those of Paraquat (Methyl Viologen) but with larger amplitude of photochemical applications.Positively and negatively charged, surfactant like, Naphthalene Diimides, were synthesized. After detailed characterization of the Naphthalene Diimides including selfassociation and interaction with surfactant molecules, the interaction with Cerium Oxide nanoparticles was determined.Naphthalene Diimides interacted in a special manner with Cerium Oxide nanoparticles rendering hydrolytic inertness and novel photochromic behavior. The organic dye is XII proposed to adsorb in the crevices of the particles and furthermore forming stable dimers that accounts for the new photoactivities observed.

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Self-assembled naphthalenediimide derivative films for light-assisted electrochemical reduction of oxygen

Abstract: This naphthalene diimide derivative, DC18, forms highly conjugated semiconducting stacked assemblies over electrodes after electrochemical conditioning. These molecular materials are very efficient towards electrochemical photoreduction of oxygen under visible light.

Cited by 16 publications

References 18 publications

Solution processed naphthalene diimide derivative as electron transport layers for enhanced brightness and efficient polymer light emitting diodes

Solution processed naphthalene diimide derivative as electron transport layers for enhanced brightness and efficient polymer light emitting diodes

Estudo das propriedades eletrônicas e espectroscópicas de uma série de diimidas naftálicas com substituintes aromáticos com potencial aplicação em dispositivos de armazenamento e conversão de energia

Novos materiais funcionais organo-híbridos baseados em óxidos metálicos e diimidas aromáticas

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