New, water-soluble BODIPY dyes have been readily obtained from various BODIPY cores by reactions involving the introduction of novel sulfonated peptide chains by either coupling or substitution to give dimethylpropargylamine derivatives subsequently quaternized by reaction with propanesultone.
Bright blue fluorescence-emitting hyperbranched polysiloxane simultaneously carrying unconjugated carbon–carbon double bonds and hydroxyl groups is reported for the first time.
Nonconventional fluorescent
polymers without π-aromatic structure
have attracted extensive interest in recent years. Hyperbranched polyesters
are generally known because of their industrial applications; however,
the luminescent properties of the polyester has not been reported.
Herein, we synthesized a series of fully biobased aliphatic hyperbranched
polyesters via a one-pot A2 + B3 esterification
reaction. Intriguingly, the resultant hyperbranched polyesters carrying
no conventional fluorescent units exhibited unexpected bright blue
fluorescence under 365 nm UV light. It was found that the fluorescence
intensity was enhanced with increasing solution concentrations and
molecular weights of the polyesters. Moreover, the results suggested
that the luminescence of polyesters could be controlled by solvents
and metal ions. In particular, the fluorescence of the polyesters
was extremely sensitive to Fe3+. More interesting is that
the fluorescence of the polyesters showed an aggregation-induced enhanced
emission in the mixture system. Notably, the resulting polyesters
displayed a remarkably enhanced quantum yield (16.75%) as compared
with that of other types of these polymers. Preliminary results demonstrate
that clustering of the carbonyl groups is responsible for the unusual
fluorescence in the aliphatic hyperbranched polyesters, namely, clustering-induced
emission (CIE). This study provides a novel perspective for the design
of biobased luminescent materials to new application areas.
A novel silicon-containing hyperbranched epoxy (SHBEp) has been explored via a one-pot A 2 + B 3 polycondensation reaction using (3-glycidyloxypropyl)trimethoxysilane (A-187) and excess neopentyl glycol (NPG) under solvent-free and catalyst-free conditions. We investigate for the first time bismaleimide (BMI) toughening effect using the fabricated polymer, and a series of SHBEp/BMI thermosets are then constructed, and then their mechanical properties like impact strength, flexural strength, and thermal stability are studied; meanwhile the toughening effect of SHBEp and conventional epoxy resin E51 is also compared. The results indicate that a proper addition of SHBEp (8 wt%) can significantly improve the toughness and thermal performance of thermosets compared to E51 with the same content. It is, therefore, revealed that the polymer is promising to act as an effective BMI toughener. Unexpectedly, a bright blue photoluminescence is observed when the SHBEp is excited under 365 nm UV light, and its average fluorescence lifetime and absolute fluorescence quantum yield are 4.30 ns and 4.61% respectively. It is demonstrated by our primary investigation that the epoxide and hydroxyl groups simultaneously help the light emission. Thus, the SHBEp bearing unconventional chromophores is also particularly expected to be a new light-emitting material. † Electronic supplementary information (ESI) available: GPC curve, the predicted 29 Si NMR of the obtained polymer, TGA and DSC curves, and additional hyperbranched polysiloxanes. See
A blue fl uorescence-emitting hyperbranched polysiloxane simultaneously containing hydroxyl and epoxy groups (HPHEp) has been developed through one-step A 2 + B 3 melt polycondensation between methoxyl groups of (3-glycidyloxypropyl)trimethoxysilane (A-187) and hydroxyl groups of neopentyl glycol under catalyst-free conditions. The emission intensity of the HPHEp in ethanol solution continuously arises in pace with raising its concentration, and the brightest luminescence is observed even in the 100% solid state. Studies show that the aggregation of oxygen-rich heteroatoms from the hydroxyl and epoxy groups is assigned to the luminous source. Intriguingly, the HPHEp displays reinforced photoluminescence after polyetherifi cation by 20 wt% polyether amine M2070; nevertheless, the modifi ed polymer represents diminished emission intensity along with increasing the polyether content. Thus, this investigation offers a new methodology of designing photoluminescent materials.
The synthesis and preliminary bio-conjugation studies of a novel water-soluble red-emitting di-styryl BODIPY dye are disclosed. Aggregation behaviour of this compound under physiological conditions was suppressed by specific introduction of a di-sulfonated peptide-based linker at the meso phenyl substituent, sultonated styryl arms and short polyethyleneglycol chains at the boron center. Thus, a good quantum yield of 22% in PBS for this red-emitting BODIPY was obtained. Introduction of an activated ester function enabled successful bio-conjugation to monoclonal antibodies and proteins.
In this Communication, novel water-soluble hyperbranched polysiloxanes (WHPSs) simultaneously containing hydroxyl and primary amine groups are developed. The polymers are constructed via melt polycondensation, that is, transesterification reaction between ethoxyl groups of (3-aminopropyl)triethoxysilane and hydroxyl groups of dihydric alcohols, using a one-step process under catalyst-free conditions. Surprisingly, the resultant WHPSs can emit bright blue fluorescence in the 100% solid state under the irradiation of UV light, and their photoluminescence intensities in aqueous solutions continuously go up along with increasing concentrations. Interestingly, their hydrolyzates display more intense luminescence compared to the unhydrolyzed. The efficient and easily controllable preparation strategy provides a remarkable and versatile platform for the fabrication of neoteric fluorescent materials for various potential applications.
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