Bisanthracene Bis(dicarboxylic imide)s as Soluble and Stable NIR Dyes

Yao, Jun; Chi, Chunyan; Wu, Jishan; Loh, Kian Ping

doi:10.1002/chem.200901398

Cited by 71 publications

(65 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Electron-withdrawing imide substituents provide an efficient means of imparting organic chromophores with acceptor-type behaviour, and thus aromatic diimides such as perylenetetracarboxylic dialkylimides and diarylimides [8] as well as their next higher rylene and bisacene homologues, that is, terrylene-, [9] quaterrylene- [10] and bisanthene-tetracarboxylic diimides, [11] are materials of great potential for organic optoelectronics.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Columnar Benzoperylene‐Hexa‐ and Tetracarboxylic Imides and Esters: Synthesis, Mesophase Stabilisation and Observation of Charge‐Transfer Interactions between Electron‐Donating Esters and Electron‐Accepting Imides

Kelber

Achard

Bonneval

et al. 2011

Chemistry A European J

View full text Add to dashboard Cite

Benzo[ghi]perylene 1,2,4,5,10,11-hexacarboxylic trialkylimide and dialkylimido-dialkyl ester derivatives, displaying a thermodynamically stable hexagonal columnar liquid-crystalline phase at room temperature, have been obtained by the use of previously unexplored chiral racemic α-branched alkylimide functions. One of the trialkylimides described here is the first room temperature columnar solely oligo-alkylimide-substituted arene, and thus constitutes a prototype case of self-assembling organic acceptor materials. As the related hexacarboxylic hexaesters are found to exhibit only a weak tendency to form columnar mesophases, benzo[ghi]perylene 1,2,5,10-tetracarboxylic tetraalkyl esters have been synthesized by regioselective oxidative Diels-Alder addition of maleic anhydride to 3,10-dicyanoperylene, and a room temperature hexagonal columnar mesophase was obtained with branched alkyl chains. The acceptor-type electronic properties of the tri- and diimides have been found to be considerably more pronounced than those of the hexa- and tetracarboxylic esters, and to approach those of the prototype acceptor material C(60). The formation of bathochromically absorbing donor-acceptor complexes was observed with a di- or triimide as acceptor and a tetraester as donor, but not with a hexaester as donor. Exploiting the non-negligible differences in reduction and oxidation potentials between all four types of materials, the minimum HOMO energy difference necessary for charge-transfer-complex formation has been determined to lie between 0.29 and 0.35 eV.

show abstract

Section: Introductionmentioning

confidence: 99%

“…Arene oligo-dicarboximides. From left to right: rylene-diimides, [8,9,10,12] bisanthene-diimide, [11] coronene-tetraimide, [13] benzoA [14,15] and laterally fused oligo-perylene-imides. [16] rated by the accompanying, albeit small, increase in clearing temperature.…”

mentioning

confidence: 99%

Columnar Benzoperylene‐Hexa‐ and Tetracarboxylic Imides and Esters: Synthesis, Mesophase Stabilisation and Observation of Charge‐Transfer Interactions between Electron‐Donating Esters and Electron‐Accepting Imides

Kelber

Achard

Bonneval

et al. 2011

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…[17] To evaluate the effects of the position of the ring-fusion on the electronic properties, cyclic voltammetry (CV) of dibenzoA C H T U N G T R E N N U N G [a,f]-fused PBI 4 a was conducted in CH 2 Cl 2 ( Figure 2) and the results, together with those reported for PBI 1 b [18] and dibenzoA C H T U N G T R E N N U N G [a,o]-fused PBI 3 a, [9] are summarized in Table 1. In the reduction process, the first reduction potential of 4 a is less negative by 0.14 V compared to that of 1 b, [18] while it is more negative by 0.22 V compared to that of 3 a.…”

mentioning

confidence: 98%

“…[8] For example, Wu and co-workers demonstrated that introduction of fused rings at the a and o bonds of the PBI core, which constructs two anthracene cores (3, Scheme 1), can cause an effective bathochromic shift in the absorption profile. [9] However, up until now, the derivatives with a p-extended structure along the short axis have been limited to only a few examples.…”

mentioning

confidence: 99%

“…[6a-c, 9,10] In this work, to understand the effects of the position of introducing fused rings, we synthesized [a,f]-fused derivatives 4 a-c, which have fused rings at both sides of the naphthalene core of the PBI, and discussed their structure-properties relationships. The syntheses of dibenzoA C H T U N G T R E N N U N G [a,f]-fused PBI 4 a and 4 c are shown in Scheme 2.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Dibenzo[a,f]perylene Bisimide: Effects of Introducing Two Fused Rings

Chaolumen

Enno

Murata

et al. 2014

Chemistry An Asian Journal

View full text Add to dashboard Cite

Perylene bisimides (PBIs) are fascinating dyes with various potential applications. To study the effects of introducing a dibenzo-fused structure to the perylene moiety, π-extended PBI derivatives with a dibenzo-fused structure at both of the a and f bonds were synthesized. The twisted structure was characterized by X-ray crystal structure analysis. In the cyclic voltammograms, the dibenzo[a,f]-fused PBI showed a reversible oxidation wave at much less positive potential, relative to a dibenzo[a,o]-fused PBI derivative. These data indicated that two ring fusions at both sides of a naphthalene moiety, which construct a tetracene core, effectively raise the HOMO level compared to fusion of one ring at each naphthalene moiety (two anthracene cores). The dibenzo[a,f]-fused PBI derivative showed an absorption band at 735 nm with a shoulder band reaching 900 nm.

show abstract