The BOPHY fluorophore with double boron chelation: Synthesis and spectroscopy

Boodts, Stijn; Fron, Eduard; Hofkens, Johan; Dehaen, Wim

doi:10.1016/j.ccr.2018.05.011

Cited by 71 publications

(39 citation statements)

References 45 publications

(72 reference statements)

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“…Another promising strategy for the production of functional optoelectronic molecular materials is the creation of dimeric molecular architectures. Several examples of 1,2‐bis((1 H ‐pyrrol‐2‐yl)methylene)hydrazines (BOPHYs) 5 and 8‐imidazodipyrromethenes ( aza ‐BOIMPYs) 6 exhibit exceptional Φ em in dilute solutions due to their relatively planar and rigid molecular geometries. BF 2 formazanate dimers 7 a and 7 b undergo emission enhancement upon dimerization at both the meta and para positions of the phenylene linkers .…”

Section: Introductionmentioning

confidence: 99%

Optoelectronic Properties of Carbon‐Bound Boron Difluoride Hydrazone Dimers

Cappello

Maar

Staroverov

et al. 2020

Chemistry A European J

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The creationo fd imericb oron difluoride complexes of chelating N-donor ligands is ap rovens trategy for the enhancement of the optoelectronic properties of fluorescent dyes. We report dimers based on the boron difluoride hydrazone (BODIHY) framework, whicho ffer uniquea nd sometimes unexpected substituent-dependent absorption, emission, and electrochemical properties. BODIHY dimers have low-energy absorption bands (l max = 421 to 479 nm, e = 17 200 to 39 900 m À1 cm À1 )t hat are red-shifted relative to monomeric analogues. THF solutionso ft hese dimers exhibit aggregation-induced emission upon additiono fw ater,w ith emissione nhancement factors ranging from 5t o1 8. Thin films of BODIHY dimers are weakly emissive as ar esult of the inner-filter effect,a ttributedt oi ntermolecular p-type interactions. BODIHY dimers are redox-active and display two one-electron oxidation and two one-electron reduction wavest hat strongly dependo nt he N-aryl substituents. These properties are rationalized using density-functional theoryc alculations and X-ray crystallography experiments. Results and Discussion Synthesis and characterizationHydrazone dimers 10 a-d were prepared by adapting al iterature procedure previously used for monomeric derivatives. [8f] This procedure involves condensationr eactionso ft he respective aryl hydrazines and 2,2'-pyridil (Scheme 1, Figures S1-S8).

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Section: Introductionmentioning

confidence: 99%

Optoelectronic Properties of Carbon‐Bound Boron Difluoride Hydrazone Dimers

Cappello

Maar

Staroverov

et al. 2020

Chemistry A European J

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“…We were interested in the fact that luminescent boron complexes, namely BOPHY, have been energetically investigated using these ligands since their discovery in 2014 (Figure 1 a). [13] Surprisingly, while there has been vigorous research on BOPHY derivatives, such as post‐modifications and π‐expansions of the skeleton, metal ion substitution has never been reported [14] . This motivated us to explore the complexation of the set of ligands ( L1 – L3 ) and aluminum ions to produce novel functional chromophores.…”

Section: Figurementioning

confidence: 99%

Dinuclear Triple‐Stranded Helicates Composed of Tetradentate Ligands with Aluminum(III) Chromophores: Optical Resolution and Multi‐color Circularly Polarized Luminescence Properties

Ono¹,

Ishihama²,

Taema³

et al. 2020

Angewandte Chemie

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New chiroptical chromophores, dinuclear triple‐stranded helicates, composed of tetradentate ligands with aluminum(III) ions, are described. These are synthesized in two steps using inexpensive pyrrole derivatives, hydrazine, and aluminum chloride. These molecular architectures (ALPHY) show multi‐color (cyan, yellow, and orange) photoluminescence in solution and in the solid‐state, which depends on the substituents of the ligands. The photoluminescence quantum yields of helicates were up to 54 %. The right‐handed (P) and left‐handed (M) helicates are so stable that they do not undergo racemization in some solvents and are mirror images according to circular dichroism and circularly polarized luminescence (CPL) with an absolute luminescence dissymmetry factor (glum) of up to the 10−3 order. Mixing the different helicates produces white‐light emission with CPL characters. This study offers a glimpse into the potential applications of chromophores with diverse photophysical properties.

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“…The growing popularity of fluorescent dyes rests upon the possibility of chemical modification of both the chromophore core and its substituents, which can manifest in a variety of spectroscopic properties [70][71][72][73][74][75][76][77][78][79][80][81][82][83]. The main objective of fluorescent BODIPY (4,4′-difluoro-4-boron-3a,4a-diaza-s-indacene) dye studies has been to explore the influence of the tautomeric equilibrium sensor on the spectroscopic parameters of the dye [84][85][86][87][88].…”

Section: Effect Of Substituents and Solvatochromism Of The Fluorescenmentioning

confidence: 99%

Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

et al. 2019

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A review of intramolecular hydrogen bonding in ortho-hydroxyaryl Schiff bases, ortho-hydroxyaryl Mannich bases, dipyrrins, ortho-hydroxyaryl ketones, ortho-hydroxyaryl amides, and 4-Bora-3a,4a-diaza-s-indacene (BODIPY) dyes with tautomeric sensors as substituents is presented in this paper. Ortho-hydroxy Schiff and Mannich base derivatives are known as model molecules for analysing the properties of intramolecular hydrogen bonding. The compounds under discussion possess physicochemical features modulated by the presence of strong intramolecular hydrogen bonds. The equilibrium between intra-and inter-molecular hydrogen bonds in BODIPY is discussed. Therefore, the summary can serve as a knowledge compendium of the influence of the hydrogen bond on the molecular properties of aromatic compounds.

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The BOPHY fluorophore with double boron chelation: Synthesis and spectroscopy

Cited by 71 publications

References 45 publications

Optoelectronic Properties of Carbon‐Bound Boron Difluoride Hydrazone Dimers

Optoelectronic Properties of Carbon‐Bound Boron Difluoride Hydrazone Dimers

Dinuclear Triple‐Stranded Helicates Composed of Tetradentate Ligands with Aluminum(III) Chromophores: Optical Resolution and Multi‐color Circularly Polarized Luminescence Properties

Intramolecular Hydrogen Bonds in Selected Aromatic Compounds: Recent Developments

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