Substituted perylene

T.K. Hatwar, J.R. Vargas, and V.V. Jarikov, Stabilized white-light-emitting OLED devices employing a stabilizing substituted perylene material, U.S. Patent 2,005,089,714, pp. 21 (2005). 

Unsymmetrically substituted perylene pigments are a comparatively recent novelty. Selective protonation of the tetra sodium salt of perylene tetracarboxylic acid affords the monosodium salt of perylene tetracarboxylic monoanhydride in high yield. Stepwise reaction with amines produces unsymmetrically substituted perylene pigments [2],... 

When the enediyne substrate has functional groups that can trap the initially formed Bergman diradical, the rapid construction of complex fused ring systems becomes feasible. J.E. Anthony and co-workers prepared an acenaphthene derivative as well as a substituted perylene using this concept. " ... 

Thus, the radical anion of naphthalene reacted differently with methyl iodide (to form methyl radicals) than with pentyl iodide (to undergo substitution). Perylene, on the other hand, underwent substitution with methyl iodide whether or not naphthalene was present perylene also underwent substitution with pentyl iodide when naphthalene was present. 

Yao, D. Tuteja, B. Sundararajan, P. R., Pigment-Mediated Nanoweb Morphology of Poly(dimethylsiloxane)-Substituted Perylene Bisimides. Macromolecules 2006, 39, 7786-7788. 

NIR fluorophores are generally considered as substances that emit fluorescence in the NIR region (650-900 nm). Particularly, the fluorescence quantum yield (QY) of NIR fluorophores is always lower than that of short wavelength emission ones. Over the past few decades, enormous progress has been made in the field of NIR fluorescent dyes. There are several major NIR organic fluorescent chromophores, such as bay-substituted perylene or naphthalene bisimides, cyanine dyes, BODIPYs, DPPs, and porphyrins. 

In this review, we restrict ourselves to metal-mediated assemblies of functional 7T-systems, which absorb light in the visible region (i.e. A. > 400 nm). Thus, materials whose color arises from metal ions or metal-ligand charge transfer (MLCT) are not included here. Self-assembhes derived from free base porphyrins, metalloporphyrins and perylene bisimide dyes have shown promising applications in artificial LH systems. Therefore, some fundamental properties of a few representative chromophores, namely meso-tetraphenylporphyrin (TPP), zinc tetraphenylporphyrin (ZnTPP), tetra-phenoxy-substituted perylene bisimide (PPBI) and bay area imsubstituted perylene bisimide (PBI), are briefly summarized herein. These properties are essential for the understanding of the photophysical and photochemical behavior of assemblies derived from such dyes. 

Tetra-amino-substituted perylene can be reacted with acid chlorides to yield tetra-N-substituted perylene 20 (Fig. 15), which form surprisingly rodshaped structures in dimethyl sulfoxide (DMSO) [50]. On the basis of X-ray data of a related compound the organization is probably controlled by amide hydrogen bonds between adjacent perylenes and the solvent. 

Figure 1.60 A schematic illustration of hydrogen-bonding of a urea substituted perylene fais-imide in its fibers [173],...

Lamotte et al. have examined the reactivity of upper electronically excited states of pyrene and perylene in liquid and solid alkane solutions. °At low temperatures, irradiation of pyrene at 185 or 248 nm in both methane and cyclohexane matrices leads to four detected photoproducts, including high yields of 1-substituted pyrenyl derivatives. Several substituted perylenes were obtained upon 185 or 248 nm irradiation in liquid and solid alkane solutions. A mechanism for alkylation of the aromatic solutes involving sequential absorption of two photons at 248 nm or one photon at 185 nm has been proposed. 

Scheme 4.21 Synthesis of bay-positions substituted perylene bisimides (i) Br2,12, H2S04 85 °C, 10 h (ii) ArNH2, Zn(OAc>2, quinoline (iii) AiOH, NMP, K2CO3, 80 °C...

Mo, X., Chen, H.Z., Shi, M.M., Wang, M. Syntheses and aggregate behaviors of liquid crystalline alkoxycarbonyl substituted perylenes. Chem. Phys. Lett. 417,457-460 (2006)... 

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