Highly Luminescent Gels and Mesogens Based on Elaborated Borondipyrromethenes

Camerel, Franck; Bonardi, Laure; Schmutz, Marc; Ziessel, Raymond

doi:10.1021/ja0606069

Cited by 182 publications

(94 citation statements)

References 17 publications

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“…Note that corresponding values for free amides usually lie at 3500-3400 cm À1 for n NH and around 1680 cm À1 for n CO . [38,39] The presence of single n NH , and n CO stretching bands in the IR spectra confirms a well-organized hydrogen-bonded network in which only one type of hydrogen bond is effective. The structure determination shows that this supramolecular hydrogen-bonded edifice adopts a V-shape.…”

Section: X-ray Characterizationmentioning

confidence: 75%

“…[24] The well-defined molecular structure of Bodipy makes it relatively easy to establish firm structure-property relationships. Recently, novel Bodipy architectures enabled their incorporation into supramolecular assemblies, such as liquid-crystalline materials or organo-gelators, [38][39][40] and luminescent phenolpyridyl-boron complexes displaying bright luminescence have been exploited in white and blue electroluminescent devices. [41] The design of luminescent and photoresponsive liquid crystals is particularly appealing owing to their potential applications in photoelectronic devices.…”

Section: Full Papermentioning

confidence: 99%

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Fine‐Tuning of Yellow or Red Photo‐ and Electroluminescence of Functional Difluoro‐boradiazaindacene Films

Bonardi

Kanaan

Camerel

et al. 2008

Adv Funct Materials

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146

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The present work describes the synthesis of difluoro‐boradiazaindacenes (Bodipy) functionalized at the central 8‐position by phenylamino moieties easily transformable into phenyl amide scaffoldings. Molecules carrying three linear or branched chains were prepared and characterized. An X‐ray crystal structure for the pivotal trimethoxyphenyl‐Bodipy derivative was determined, and the packing is discussed in terms of molecular interactions; a key feature for the formation of thin films. All of the dyes are thermally stable up to 170 °C but no liquid‐crystalline phases are observed. Reversible reduction and oxidation processes occur around +0.97 and −1.34 V, respectively, versus saturated calomel electrode in solution and the electroactivity and photoluminescence are maintained in thin films produced by vacuum evaporation. Interestingly, two distinct emissions are observed at 550 and 635 nm by electroluminescence of the trimethoxyphenyl‐Bodipy derivative, corresponding to the luminescence of isolated molecules and dimers, respectively. Doping Alq3 films with this Bodipy molecule by vacuum evaporation produces organic light‐emitting diodes (OLEDs) in which very efficient energy transfer from the Alq3 matrix to the Bodipy occurs by a resonance mechanism involving the first Bodipy excited state. Yellow light (550 nm, 344 cd m−2 at 15 V) is emitted at low doping concentration (7 mol %), whereas red light (635 nm, 125 cd m−2 at 15 V) is emitted at higher concentration (19 mol %). Dispersion of the Bodipy into a fluorescent poly(N‐vinylcarbazole) polymer (PVK) (≈3 mol % per repeating unit of PVK) by solution processing exclusively produces yellow emission owing to the isolated Bodipyfluorophore (550 nm, 213 cd m−2 at 15 V). The second excited state of the Bodipy dye is likely involved during energy transfer from the PVK matrix.

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Section: X-ray Characterizationmentioning

confidence: 75%

Section: Full Papermentioning

confidence: 99%

Fine‐Tuning of Yellow or Red Photo‐ and Electroluminescence of Functional Difluoro‐boradiazaindacene Films

Bonardi

Kanaan

Camerel

et al. 2008

Adv Funct Materials

Self Cite

146

View full text Add to dashboard Cite

show abstract

“…For example, the Bodipy derivative 9 has been reported to form a gel in a nonpolar solvent like n-nonane (Figure 4). 52 The gelator 9 is designed in such a way that the methyl substituent at the central phenyl ring forces the adjacent amide units to tilt at a certain angle and thereby facilitate intermolecular H-bonding. Upon cooling from an isotropic melt, 9 exhibited pseudo-fan shaped texture with large homotropic domains, characteristic of columnar LC phase (Figure 4c-e) followed by a room temperature crystalline state.…”

Section: Bodipy-derived Supramolecular Gelatorsmentioning

confidence: 99%

Self-Assembly of Bodipy-Derived Extended π-Systems

Cherumukkil

Vedhanarayanan

Das

et al. 2017

Bulletin of the Chemical Society of Japan

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Self-assembly is a viable approach to create soft functional materials with architectural diversity and property variations. Among the large number of different chromophores used, borondipyrromethene (Bodipy) dyes find a unique space because of their promising photophysical properties such as high molar absorptivity, fluorescent quantum yield and excellent photostability along with the associated synthetic ease. Recently, research on Bodipy dyes has experienced a surge of activities in view of favorable self-assembling properties. In this review, recent developments in self-assembled Bodipy dyes and their significance in various applications are discussed.

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“…These results are similar to those reported for molecular J-aggregates in which the excitonic energy is delocalized as a result of intermolecular coupling within the head-to-tail arrangement of the molecules in the solution. [35] The compounds exhibit fluorescence in the solid state also. The optical band gaps E g of both compounds were determined from their absorption in thin solid film following the method of reference.…”

Section: Photophysics and Photophysical Properties In Solutionsmentioning

confidence: 99%

Fluorescence Confocal Polarizing Microscopy of a Fluorescent Bent‐Core Liquid Crystal Exhibiting Polarization Splay Modulated (B7) Structures and Defects

et al. 2014

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The B7 phases of bent-core molecules are polarization splay modulated fluid smectics that exhibit an unusually complex variety of exotic macroscopic structures, textures, and defects visible in polarized light microscopy. Herein we describe optical studies of these structures using fluorescence confocal polarizing microscopy (FCPM) and depolarized transmission optical microscopy to probe their organization in three dimensions. These experiments utilize recently reported fluorescent bent-core molecules designed to give strong polarized fluorescence. This new bent-core molecular family provides the means for probing a variety of bent-core phases and structures by using FCPM and multiphoton fluorescence nonlinear imaging techniques. Comparative textural analysis of the B7 structures obtained using different types of imaging and the corresponding structural models are discussed.

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Highly Luminescent Gels and Mesogens Based on Elaborated Borondipyrromethenes

Cited by 182 publications

References 17 publications

Fine‐Tuning of Yellow or Red Photo‐ and Electroluminescence of Functional Difluoro‐boradiazaindacene Films

Fine‐Tuning of Yellow or Red Photo‐ and Electroluminescence of Functional Difluoro‐boradiazaindacene Films

Self-Assembly of Bodipy-Derived Extended π-Systems

Fluorescence Confocal Polarizing Microscopy of a Fluorescent Bent‐Core Liquid Crystal Exhibiting Polarization Splay Modulated (B7) Structures and Defects

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