Supramolecular Construction of Fluorescent J‐Aggregates Based on Hydrogen‐Bonded Perylene Dyes

Kaiser, Theo E.; Wang, Hao; Stepanenko, Vladimir; Würthner, Frank

doi:10.1002/ange.200701139

Cited by 147 publications

(68 citation statements)

References 37 publications

(13 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The use of Br 2 -PTCDI provides the first demonstration of a route to functionalise the cavities of the PTCDI/melamine regular hexagonal arrangement. It is worth noting that Br 2 -PTCDI is a synthetic precursor to a range of R 2 -PTCDI molecules [25] and as such the Br 2 -PTCDI/melamine array offers the potential for further chemical functionalisation.…”

Section: Surface Studiesmentioning

confidence: 99%

Functionalized Supramolecular Nanoporous Arrays for Surface Templating

Perdigão

Saywell

Fontes

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

Controlled self-assembly and chemical tailoring of bimolecular networks on surfaces is demonstrated using structural derivatives of 3,4:9,10-perylenetetracarboxylic diimide (PTCDI) combined with melamine (1,3,5-triazine-2,4,6-triamine). Two functionalised PTCDI derivatives have been synthesised, Br(2)-PTCDI and di(propylthio)-PTCDI, through attachment of chemical side groups to the perylene core. Self-assembled structures formed by these molecules on a Ag-Si(111)sqrt3 x sqrt3R30 degrees surface were studied with a room-temperature scanning tunneling microscope under ultrahigh vacuum conditions. It is shown that the introduction of side groups can have a significant effect upon both the structures formed, notably in the case of di(propylthio)-PTCDI which forms a previously unreported unimolecular hexagonal arrangement, and their entrapment behaviour. These results demonstrate a new route of functionalisation for network pores, opening up the possibility of designing nanostructured surface structures with chemical selectivity and applications in nanostructure templating.

show abstract

Section: Surface Studiesmentioning

confidence: 99%

Functionalized Supramolecular Nanoporous Arrays for Surface Templating

Perdigão

Saywell

Fontes

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The emission wavelength is red-shifted by 17 nm relative to that of monomer 3, and the fluorescence quantum yield drops to almost one third of the monomer, which is obviously different from that observed for the typical "J-type" aggregates [6] [7]. The fluorescence lifetime increases slightly from 6.1 ns for the monomer 3 to 7.8 ns for dimer 8.…”

Section: Fluorescence Spectra and Fluorescence Lifetimementioning

confidence: 58%

“…The fluorescence lifetime increases slightly from 6.1 ns for the monomer 3 to 7.8 ns for dimer 8. The Stokes shift of the emission band is 36 nm, which is also significantly larger than that observed for the typical "J-type" aggregates [6]- [8]. All the characteristics of the emission of dimer 8 as mentioned above suggest that the 620 nm emission can be assigned to the "excimer-like" state of dimer 8.…”

Section: Fluorescence Spectra and Fluorescence Lifetimementioning

confidence: 67%

See 1 more Smart Citation

Photophysical Properties of Perylenetetracarboxylic Diimide Dimers with Slipped “Face-to-Face” Stacked Structure and Different Bay Substitutions

Qingdao¹

2016

MSCE

View full text Add to dashboard Cite

A series of perylenetetracarboxylic diimides (PDIs) dimers with slipped "face-to-face" stacked structure and different substituents at the bay positions have been synthesized and the molecular structures are characterized by 1 H NMR, MALDI-TOF and elemental analysis. And different substituents at the bay positions of the PDI ring bring about various steric hindrances. These different steric hindrances have caused significant differences on the absorption and emission spectra. The correlation between the photophysical properties and the molecular structure is discussed.

show abstract

“…[6] Diese Fibrillen zeigen photoinduzierten Elektronentransfer und können auch als "Doppelkabel"-Nanodrähte aufgefasst werden. Weitere Beispiele umfassen flüssigkristalline Phasen von Perylenbisimiden, die terminal mit sterisch anspruchsvollen Tris(dodecyloxy)phenyl-Einheiten substituiert sind, [7] Organogele aus verwandten H-verbrückten Derivaten [8] sowie helicale Fibrillen von Perylenbisimiden, welche die Tris(dodecyloxy)phenyl-Einheiten in der "Bucht-Region" (1,6,7,12-Positionen) tragen; [9] diese Fibrillen bildeten stark fluores- [11] Auch die metallorganische Koordinationschemie wurde für die Herstellung supramolekularer Aggregate und Materialien genutzt. Entsprechende Arbeiten umfassen koordinativ gebundene Makrocyclen, [12] metallorganische Koordinationspolymere, [13] hierarchisch strukturierte Materialien aus gefalteten Polymeren, [14] Polyrotaxane [15] und zweidimensionale Gitter.…”

unclassified