Excitonic Coupling in Acyclic and Cyclic Dithioaryl‐Linked BODIPY DYEmers

Ahrens, Johannes; Scheja, Anne; Wicht, Richard; Bröring, Martin

doi:10.1002/ejoc.201600359

Cited by 21 publications

(14 citation statements)

References 60 publications

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“…In the case of BODIPY dyes, it has been well documented in a wide range of derivatives that dispersion within a polymer matrix or deposition of pure films results in significant PL quenching accompanied by spectral shifts. 9,10,[12][13][14][15][16][17][18][19][20][21] Analogous effects have also been described in a wide range of covalent dimers, 11,15,[21][22][23][24][25][26] though the geometries are typically a poor match for the structures obtained in the solid state. Quenching in these systems is often attributed to the formation of non-emissive H-aggregates, identified by a broadening of the absorption spectrum at higher energies.…”

Section: Introductionmentioning

confidence: 88%

“…Quenching in these systems is often attributed to the formation of non-emissive H-aggregates, identified by a broadening of the absorption spectrum at higher energies. 10,[15][16][17]26,27 Red-shifted PL spectral features have been variously attributed to excimers and J-aggregates, typically on the basis of their spectral position alone. 6,9,[12][13][14][19][20][21][22][23][24] The properties of these emissive states have not been analyzed in detail, nor the mechanism of their formation.…”

Section: Introductionmentioning

confidence: 99%

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Intermolecular states in organic dye dispersions: excimers vs. aggregates

et al. 2017

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Section: Introductionmentioning

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Intermolecular states in organic dye dispersions: excimers vs. aggregates

et al. 2017

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“…However, the broad fluorescence profile as well as the biexponential dynamics of the excited state of 2 a do not allow to reject a priori the formation of a stronger aggregate, which could be described as an excimer . Although excimer formation is not straightforward in view of the ground‐state calculations, small conformational changes upon excitation can deeply alter the excitonic coupling assisting excimer formation, which can even coexist with intramolecular J‐type aggregates, and this leads to complex excited‐state dynamics. In fact, a closer inspection of the fluorescence spectrum reveals a shoulder at higher energies, the intensity of which depends on the excitation wavelength (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Stereochemical and Steric Control of Photophysical and Chiroptical Properties in Bichromophoric Systems

Blázquez-Moraleja

Cerdán

García‐Moreno

et al. 2018

Chemistry A European J

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Stereochemical and steric control of the relative spatial arrangement of the chromophoric units in multichromophoric systems offers an interesting strategy for raising unusual and appealing light-induced emission states. To explore and exploit this strategy, a series of conformationally restricted boron-dipyrromethene (BODIPY) dimers were designed by using tartaric acid as a symmetrical connector between the boron atoms of the dyes. The variety of stereoisomeric forms available for this bis(hydroxy acid) allows the relative spatial orientation of the chromophoric units in the dimer to be modified, which thus opens the door to modulation of the photophysical and chiroptical properties of the new bichromophoric systems. Chromophore alkylation introduces an additional level of control through distance-dependent steric interactions between the BODIPY units in the dimer, which also modulates their relative spatial disposition and properties.

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“…Various macrocycles with unique properties were synthesized by altering the linking unit between the BODIPY nuclei and by changing the number of repeating units. [56][57][58][59][60][61][62][63][64][65] In particular, Nabeshima and coworkers focused on the unique shapes and the molecular recognition properties of the cyclic BODIPY oligomers. As already mentioned, the fluorine atoms of the BF 2 unit are negatively charged, and they can interact with a cationic molecule such as ammonium ions.…”

Section: Scheme 2 Synthesis Of Selenophenyl Bodipy Oligomers 3 Cyclicmentioning

confidence: 99%

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Chiba¹,

Nakamura²,

Matsuoka³

et al. 2020

Synlett

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The dipyrrin–metal complexes and especially the boron complex 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) have recently attracted considerable attention because of their interesting properties and possible applications. We have developed two unique and useful ways to extend versatility and usefulness of the dipyrrin complexes. The first one is the linear and macrocyclic oligomerization of the BODIPY units. These arrangements of the B–F moieties of the oligomerized BODIPY units provide sophisticated functions, such as unique recognition ability toward cationic guest, associated with changes in the photophysical properties by utilizing unprecedented interactions between the B–F and a cationic species. The second one is introduction of additional ligating moieties into the dipyrrin skeleton. The multidentate N2Ox dipyrrin ligands thus obtained form a variety of complexes with 13 and 14 group elements, which are difficult to synthesize using the original N2 dipyrrin derivatives. Interestingly, these unique complexes exhibit novel structures, properties, and functions such as guest recognition, stimuli-responsive structural conversion, switching of the optical properties, excellent stability of the neutral radicals, etc. We believe that these multifunctional dipyrrin complexes will advance the basic chemistry of the dipyrrin complexes and develop their applications in the materials and medicinal chemistry fields.1 Introduction2 Linear Oligomers of Boron–Dipyrrin Complexes3 Cyclic Oligomers of Boron–Dipyrrin Complexes4 A Cyclic Oligomer of Zinc–Dipyrrin Complexes5 Group 13 Element Complexes of N2Ox Dipyrrins6 Chiral N2 and N2Ox Dipyrrin Complexes7 Group 14 Element Complexes of N2O2 Dipyrrins8 Other N2O2 Dipyrrin Complexes with Unique Properties and Functions9 Conclusion

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Excitonic Coupling in Acyclic and Cyclic Dithioaryl‐Linked BODIPY DYEmers

Cited by 21 publications

References 60 publications

Intermolecular states in organic dye dispersions: excimers vs. aggregates

Intermolecular states in organic dye dispersions: excimers vs. aggregates

Stereochemical and Steric Control of Photophysical and Chiroptical Properties in Bichromophoric Systems

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

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