DPP Dyes as Ligands in Transition-Metal Complexes

Lorenz, Ingo‐Peter; Limmert, Michael E.; Mayer, Péter; Piotrowski, Holger; Langhals, Heinz; Poppe, Martin; Polborn, Kurt

doi:10.1002/1521-3765(20020902)8:17<4047::aid-chem4047>3.0.co;2-m

Cited by 30 publications

(17 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structure of the isatin‐gold complex was determined by X‐ray diffraction . Similar gold(I) complexes have been reported with the anions of hydantoin, of PPP dyes and of various other N‐heterocycles…”

Section: Modern Coordination Chemistry Of Indigo and Its Substitutesupporting

confidence: 61%

Metal Complexes of Indigo and of Some Related Ligands

Beck

Sünkel

2020

Zeitschrift anorg allge chemie

View full text Add to dashboard Cite

While the first coordination compounds of indigo were reported over 100 years ago, a systematic study of the coordination chemistry of this important dye and also its structural “relatives” remained silent for over half a century. Only in the last two decades of the 20th century research on this topic started again keeps on growing ever since. It could be established, mainly by X‐ray crystallography, but also by many other modern spectroscopic techniques, that deprotonated indigo, and its deprotonated oxidized and reduced forms act as mono‐ and bidentate chelate ligands in metal complexes

show abstract

Section: Modern Coordination Chemistry Of Indigo and Its Substitutesupporting

confidence: 61%

Metal Complexes of Indigo and of Some Related Ligands

Beck

Sünkel

2020

Zeitschrift anorg allge chemie

View full text Add to dashboard Cite

show abstract

“…Analogous complexes with more demanding groups than CN t Bu, as PEt 3 or PPh 3 , do not exhibit aurophilic interactions [336]. These complexes are interesting because of their properties, the dye ligand diketopyrrolopyrrole is luminescent but the coordination to gold (and also to other metals such as silver, copper, palladium or platinum) leads to 3 ] with the acceptors 2,4,7-trinitro-9-fluorenone and 2,3,4,7-tetranitro-9-fluorenone consist of columns of planar molecules showing the pattern Á Á Ádonor-acceptor-donor-acceptorÁ Á Á Compound [Au 3 (EtOC¼NpTol) 3 ] interacts with octafluoronaphthalene to form an adduct which crystallizes with the same pattern.…”

Section: Complexes With Bridging Bidentate Ligandsmentioning

confidence: 99%

Gold–Gold Interactions

Crespo

2008

Modern Supramolecular Gold Chemistry

View full text Add to dashboard Cite

This chapter focuses mainly on closed shell gold(I) atoms which are found to feel attraction among themselves. This attraction is able to modify expected geometries or support one-, two-or three-dimensional arrays and also leads to interesting properties. Closed shell metal cations are expected to repel each other. Nevertheless, an important number of examples containing [d 8 -d 10 -s 2 ] interactions are known. Particularly strong evidence has been accumulated on the attraction between two or more d 10 shells. In the case of gold(I) such attraction between two or more monovalent gold(I) ions in compounds has been observed structurally for a long time. In these situations the gold centers approach each other to a distance of between 2.7 and 3.3 Å. This range includes the distance between gold atoms in gold metal and approaches, or even overlaps with the range of distances found in the few real Au-Au single bonds. Schmidbaur coined the name aurophilic attraction in 1990 and defined it as the unprecedented affinity between gold atoms even with closed-shell electronic configurations and equivalent electrical charges [1]. Since that moment, aurophilicity has become one of the hot topics in gold chemistry, at first with the aim of understanding such interaction, more recently because of the observation that it may play an important role in interesting properties, thus understanding and modulating aurophilic interactions could help to govern these properties, which include the optical behavior. Although different origins are possible for the luminescent emissions of coordination complexes, such as intraligand transitions (ILT), ligand to metal or metal to ligand charge transfer transitions (LMCT, MLCT) and metal centered (MCT) transitions, in many luminescent gold complexes the emissions have been related to the presence of aurophilic interactions.Information about aurophilicity and chemical situations in which it is observed may be found in different works that may be classified as those which analyse closed shell interactions in general [2], those focused on aurophilicity [1,3], and others which analyze the role of these interactions in coordination [4] and organometallic gold Modern Supramolecular Gold Chemistry: Gold-Metal Interactions and Applications. Edited by Antonio Laguna

show abstract

“…Recently its derivatives and polymers have been widely studied in such fields as organic thin film transistors,6 light‐emitting diodes,7 and dye‐sensitized solar cells,8 and above‐all, bulk‐heterojunction solar cells 9–11. Synthetic advances, pioneered by Langhals and co‐workers,12a–h are continuing to strive, offering new easy tools to modify the chromophore and its inversed analogue: Pyrrolo[3,2‐ b ]pyrrole‐2,5(1 H ,4 H )‐dione (iDPP) 12. Altering aryl substituents offers rather small shifts of absorption and emission.…”

Section: Introductionmentioning

confidence: 99%

Two‐Photon‐Induced Fluorescence in New π‐Expanded Diketopyrrolopyrroles

Grzybowski

Hugues

Blanchard‐Desce

et al. 2014

Chemistry A European J

View full text Add to dashboard Cite

Structurally unique π-expanded diketopyrrolopyrroles (EDPP) were designed and synthesized. Strategic placement of a fluorene scaffold at the periphery of a diketopyrrolopyrrole through tandem Friedel-Crafts-dehydration reactions resulted in dyes with supreme solubility. The structure of the dyes was confirmed by X-ray crystallography verifying a nearly flattened arrangement of the ten fused rings. Despite the extended ring system, the dye still preserved good solubility and was further functionalized by using Pd-catalyzed coupling reactions, such as the Buchwald-Hartwig amination. Photophysical studies of these new functional dyes revealed that they possess enhanced properties when compared with expanded DPPs in terms of two-photon absorption cross-section. It is further demonstrated that in addition to the initial diacetals, the final electrophilic cyclization step can also be applied to diketones. By placing two amine groups at peripheral positions of the resulting dyes, values of two-photon absorption cross-section on the level of 2000 GM around 1000 nm were achieved, which in combination with high fluorescence quantum yield (Φfl ), generated a two-photon brightness of approximately 1600 GM. These characteristics in combination with strong red emission (665 nm) make these new π-expanded diketopyrrolopyrroles of major promise as two-photon dyes for bioimaging applications. Finally, the corresponding N-alkylated DPPs displayed a solid-state fluorescence.

show abstract

DPP Dyes as Ligands in Transition-Metal Complexes

Cited by 30 publications

References 8 publications

Metal Complexes of Indigo and of Some Related Ligands

Metal Complexes of Indigo and of Some Related Ligands

Gold–Gold Interactions

Two‐Photon‐Induced Fluorescence in New π‐Expanded Diketopyrrolopyrroles

Contact Info

Product

Resources

About