Nanoparticles via H-aggregation of amphiphilic BODIPY dyes

Tokoro, Yuichiro; Nagai, Atsushi; Chujo, Yoshiki

doi:10.1016/j.tetlet.2010.04.120

Cited by 68 publications

(45 citation statements)

References 18 publications

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“…On the other hand, the H‐aggregation of BODIPY chromophores normally induces a marked decrease in the molar extinction coefficient and a broad band in the shorter‐wavelength region. Such a phenomenon was previously observed with azaBODIPY derivatives, and BODIPY derivatives with π‐conjugate moieties linked at the 2,6‐positions . Thus, the interactions in DBT and DB are not due to intramolecular H‐aggregation of the BODIPY chromophores.…”

Section: Resultssupporting

confidence: 70%

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Unexpected Nucleophilic Substitution Reaction of BODIPY: Preparation of the BODIPY–TEMPO Triad Showing Radical‐Enhanced Intersystem Crossing

Суханов

Zhao

et al. 2018

Eur J Org Chem

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We have discovered a new and unexpected substitution reaction of BODIPY. Through single‐crystal XRD analysis, DFT calculations, and other complimentary spectroscopic methods, we have confirmed that the molecular structural assignment of the previously reported nucleophilic substitution of the halogenated carbon atom at the meso position of BODIPY was inaccurate. Indeed, in these substitution reactions, the amino attaches to the methyl group at the 3‐ or 5‐position and not on the meso‐carbon of the BODIPY core. As a result of this unexpected substitution reaction, we prepared a BODIPY dimer, attached to the stable radical TEMPO (2,2,6,6‐tetramethyl‐1‐piperidinyloxyl). We confirmed the efficient formation of the triplet state (ΦΔ = 59 %, τT = 2.8 µs) of this BODIPY–TEMPO triad through the radical‐enhanced intersystem crossing mechanism by using nanosecond time‐resolved transient absorption spectroscopy. Through time‐resolved EPR spectroscopy, the doublet (spin angular momentum quantum number S = 1/2) and quartet (S = 3/2) states of the triad were observed. Moreover, we observed a strong intramolecular ground‐state interaction between the BODIPY chromophores in the triad, which shows new spectral features different to those of H‐ or J‐aggregates and the exciton coupling effect. These TEMPO‐labeled compounds were used as triplet photosensitizers for triplet–triplet annihilation (TTA) upconversion (quantum yield ΦUC = 4.7 %).

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Section: Resultssupporting

confidence: 70%

“…Interestingly, we found that the UV/Vis absorption profiles of DB and DBT are different to those caused by exciton coupling, or J‐ or H‐aggregation of BODIPY chromophores . Moreover, the spectral changes due to the ground‐state interaction are also different to those of BODIPY dimers with co‐facial geometries …”

Section: Resultsmentioning

confidence: 83%

Unexpected Nucleophilic Substitution Reaction of BODIPY: Preparation of the BODIPY–TEMPO Triad Showing Radical‐Enhanced Intersystem Crossing

Суханов

Zhao

et al. 2018

Eur J Org Chem

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“…[14] The absorption onset at about 815 nm corresponds to an optical band gap of 1.52 eV, slightly above the value for TB2 (i.e. 1.45 eV).…”

Section: 1002/cssc201700465 Chemsuschemmentioning

confidence: 83%

Rational Engineering of BODIPY‐Bridged Trisindole Derivatives for Solar Cell Applications

et al. 2017

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Boron dipyrromethene (BODIPY) and its derivatives are known to be efficient photon-harvesting chromophores. However, their study as active materials in bulk heterojunction (BHJ) solar cells is still scarce. In this study, the development of new synthetic ways to design original BODIPY-based dumbbell-shape molecules, including a first 2,3,5,6-tetravinyl aromatic BODIPY molecule, is reported. High fill factors can be obtained in BHJ solar cells when blended with a fullerene derivative, leading to a new record BODIPY-based power conversion efficiency of 5.8 %.

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“…To this end, we have selected a4 ,4difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) [14] core not only for its small size and planarity but also due to its wellknown ability to self-assemble in an H- [15] or J-type [16] fashion, which can be readily investigated by common spectroscopic methods. To this end, we have selected a4 ,4difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) [14] core not only for its small size and planarity but also due to its wellknown ability to self-assemble in an H- [15] or J-type [16] fashion, which can be readily investigated by common spectroscopic methods.…”

Section: Introductionmentioning

confidence: 99%

Influence of Ester versus Amide Linkers on the Supramolecular Polymerization Mechanisms of Planar BODIPY Dyes

Rödle

Ritschel

Mück‐Lichtenfeld

et al. 2016

Chemistry A European J

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We report the H-type supramolecular polymerization of two new hydrophobic BODIPY derivatives equipped with ester and amide linkages. Whereas the ester-containing BODIPY derivative undergoes an isodesmic supramolecular polymerization in which the monomers are parallel-oriented, the replacement of the ester by amide groups leads to a highly cooperative self-assembly process into H-type aggregates with a rotational displacement of the dye molecules within the stack. The dye organization imposed by simultaneous π-π and hydrogen bonding interactions is the driving force for the cooperative supramolecular polymerization, whereas the absence of additional hydrogen bonds for the ester-containing moiety does not suffice to induce cooperative phenomena.

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Nanoparticles via H-aggregation of amphiphilic BODIPY dyes

Cited by 68 publications

References 18 publications

Unexpected Nucleophilic Substitution Reaction of BODIPY: Preparation of the BODIPY–TEMPO Triad Showing Radical‐Enhanced Intersystem Crossing

Unexpected Nucleophilic Substitution Reaction of BODIPY: Preparation of the BODIPY–TEMPO Triad Showing Radical‐Enhanced Intersystem Crossing

Rational Engineering of BODIPY‐Bridged Trisindole Derivatives for Solar Cell Applications

Influence of Ester versus Amide Linkers on the Supramolecular Polymerization Mechanisms of Planar BODIPY Dyes

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