Highly fluorescent water-soluble polyglycerol-dendronized perylene bisimide dyes

Abstract

Water-soluble perylene tetracarboxylic acid bisimides (PBIs) with terminally linked polyglycerol dendrons of four different generations have been synthesized. These PBI dyes reveal a strong dendritic effect, enabling outstanding fluorescence quantum yields in water up to almost 100% for the highest dendron generation.

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

“…It is a gratifying situation that researchers from industry published a significant number of crystal structures and empirical correlations between packing structures and coloristic properties ( Figure 5). 70−74 For 18 PBI compounds bearing different imide substituents (but no core modifications), including industrially relevant color pigments, these authors distinguished two main classes: pigments of red or maroon shade characterized by small longitudinal offsets (e.g., the brilliant red Pigment Red 178 bearing azobenzene substituents at the imide nitrogens and the maroon Pigment Red 179 bearing methyl substituents) and pigments of black shades characterized by pronounced longitudinal shifts (e.g., Pigment Black 31 bearing phenethyl substituents). In all cases, the PBI scaffold is planar, and no additional visible absorption bands are attributable to the imide substituents.…”

“…Thus, the subsequent fourth reduction to the tetraanion 2-18 4− could be achieved at less negative potential as the Coulomb repulsions in the ring widened cyclophane are significantly reduced. 193 Most recently, Spenst and Wurthner have reported the first example of a para-xylylene bridged PBI cyclophane (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) that encapsulates a large variety of aromatic guest molecules in its cavity leading to the respective 1:1 host−guest complexes. 194 A unique functional feature of this novel PBI cyclophane is the tunability of its emission depending on the electronic nature of the encapsulated aromatic guests.…”

“…For this reason, macrocycles constituted the preferred class of supramolecular hosts as demonstrated by crown ethers, cryptands, and carcerands from the early beginning. 189−191 The structures of a selection of PBI cyclophanes with dodecylene (2-17), phenylene-ethynylene (2-18), or para-xylylene (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) linkages, or very rigid s-triazinylene (2-20a−c) or phenylene bridges (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21), are displayed in Chart 5.…”

Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

“…Therefore, several attempts have been performed in order to increase their solubility in aqueous media, either with functionalization in the bay region [12][13][14][15][16] or at the side imide groups. [17][18][19][20][21][22][23][24][25] Recently, we have introduced a series of highly water-soluble PBIs containing anionic (R 1 ) or cationic (R 2 ) Newkome dendronized substituents -representative examples are given in Fig. 1.…”

Synthesis and Characterization of Alternating Polymers Incorporating Boron-Chelated Heterochrysene Units

“…BF 2 -poly and BPh 2 -poly showed obvious bathochromic-shift compared to the corresponding compounds. The quantum yields (Φf) of BF 2 -poly and BPh 2 -poly were calculated as 0.23 and 0.11, respectively, where N,N'-di(2,6-diisopropylphenyl)-perylene-3,4,9,10-tetracarboxylic acid bisimide (Φf = 1.00 in chloroform) was used as the reference standard [29]. It should be noted that boron-chelated polymers exhibited decreased fluorescence quantum compared to those of 1 and 2, respectively.…”