- Twisting strategy applied to N,N-diorganoquinacridones leads to organic chromophores exhibiting efficient solid-state fluorescence
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A new molecular design of organic emitters exhibiting efficient solid-state fluorescence, which involves planarity breaking of N,N-diorganoquinacridones, is presented. The new design principle led to the development of dimethyl 2,5-diaminoterephthalates and 2,5-diamino-1,4-diaroylbenzenes, which emitted green to yellow and yellow to red light with high-to-excellent quantum yields, respectively. In addition, the photoluminescence properties of the diaroylbenzenes were dependent on the morphology and reversibly variable by thermal and solvent vapor stimuli.
- Shimizu, Masaki,Asai, Yuiga,Takeda, Youhei,Yamatani, Akinori,Hiyama, Tamejiro
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supporting information; experimental part
p. 4084 - 4089
(2011/09/19)
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- Quinacridone derivatives as labelling reagents for flurescence detection of bilogical materials
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Disclosed are new quinacridone dye derivatives having characteristic fluorescence lifetimes. Also disclosed are methods for labelling target biological materials employing the quinacridone dyes and use of the labelled materials in biological assays. The quinacridone derivatives have the structure (I), in which Z1 and Z2 independently represent the atoms necessary to complete one ring, two fused ring, or three fused ring aromatic or heteroaromatic systems, each ring having five or six atoms selected from carbon atoms and optionally no more than two atoms selected from oxygen, nitrogen and sulphur; R3, R4, R5, R6, R7 and R8 are independently selected from hydrogen, halogen, amide, hydroxyl, cyano, nitro, mono- or di-nitro-substituted benzyl, amino, mono- or di-C1-C4 alkyl-substituted amino, sulphydryl, carbonyl, carboxyl, C1-C6 alkoxy, acrylate, vinyl, styryl, aryl, heteroaryl, C1-C20 alkyl, aralkyl, sulphonate, sulphonic acid, quaternary ammonium, the group —E—F and the group —(CH2—)nY; R1 and R2 are independently selected from hydrogen, mono- or di-nitro-substituted benzyl, C1-C20 alkyl, aralkyl, the group —E—F and the group —(CH2—)nY; E is a spacer group, F is a target bonding group; Y is selected from sulphonate, sulphate, phosphonate, phosphate, quaternary ammonium and carboxyl; and n is an integer from 1 to 6. The invention also relates to a set of different fluorescent quinacridone dye derivatives, each dye having a different fluorescence lifetime, the set of dyes being particularly useful for multiparameter analysis. 1
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