Cyclic Carboxylic Imide Structures as Structure Elements of High Stability. Novel Developments in Perylene Dye Chemistry

Abstract

-Cyclic carboxylic imides are structure elements in aromatic heterocycles with high persistency. Their attachment to perylene leads to the perylene dyes; the synthesis and unique properties of the dyes are reported and discussed. An extension of the principle to other aromatics is made.

Imaging perylene derivatives on rutileTiO2(110)by noncontact atomic force microscopy

“…Besides 3,4,9,10-perylene tetracarboxylic acid-dianhydride ͑PTCDA͒, a great number of other perylene derivatives have been studied, including 3,4,9,10-perylene tetracarboxylic diimine ͑PTCDI͒. 4,5 These molecules have been deposited on various conducting surfaces including Ag, Au, Cu, and highly oriented pyrolytic graphite [6][7][8][9][10][11][12][13][14][15][16][17][18] as well as semiconducting [19][20][21][22] and insulating substrates such as KBr, KCl, NaCl, and mica. [23][24][25][26][27][28] Titanium dioxide plays a prominent role due to its promising properties for a wide range of various applications such as catalysis and solar cells.…”

Restricted conformation dynamics of single functionalized perylene bisimide molecules on SiO2surfaces and in thin polymer films

“…In a recent publication [11] a comparison of time resolved fluorescence and molecular dynamics calculations has demonstrated, that these bay groups control the formation and interconversion of two limiting classes of conformations. Additionally, different conformations might give rise to twisting of the perylene core itself [12,13]. It is evident, that the realisation of conformations and the related dynamics will be controlled by external restrictions such as embedding into various polymers [14,15].…”

Energy transfer in pendant perylene diimide copolymers

“…Aggregation is greatly decreased by functionalising the diimide end-groups with bulky substituents that impede cofacial π-π interactions between the PDIs. [20][21][22][23][24][25][26][27] Accordingly the imide substituents can be used to control solubility and decrease aggregation without impacting the photophysical properties of the PDI chromophore. 28 Nevertheless, imide substituted perylenes still aggregate at FRET-enabling concentrations, 29 and thus aggregation remains a limiting factor inhibiting efficient FRET in PDI based LSCs.…”