Abstract:This review focuses on side-chain functionalized polymers derived from direct (co)polymerization of fluorescent dyes. This overview about polymerizable dyes includes 1,8-naphthalimides, fluoresceins, rhodamines, coumarins, azo-dyes, oxadiazoles, diverse aromatic dyes as well as selected other dyes that cannot be classified within these groups. The discussed dyes have been functionalized with a polymerizable unit in order to apply straight-forward polymerization procedures. Therefore, the center of attention is… Show more
“…Mainly two approaches have been utilized to incorporate fluorescent dyes into polymeric materials: physical blending [18][19][20][21] and chemical linkage. 5,22,23 Physically mixing organic dyes into polymers has advantage of attaining new properties without synthesizing new polymer structures. Fluorescence quenching induced by phase separation, however, can occur when the dye is not compatible in the polymer matrix.…”
Well-defined 1,4-diketo-3,6-di(thiophen-2-yl)pyrrolo [3,4-c]pyrrole (DTDPP) labeled polycaprolactones (PCL) with different chain lengths were synthesized and characterized. The effect of polymer chain lengths on the optical properties of DTDPP in solid states was studied by UV-Vis absorption spectroscopy as well as steady-state and dynamic fluorescence spectroscopies. Our results indicate that when the PCL side chain is extended to a certain length, the intermolecular aggregation of DTDPP units can be reduced significantly due to segregation effect of PCL. This approach offers a new facile strategy to address the common problem of aggregationcaused quenching existing in organic fluorophores. These highly fluorescent biodegradable PCL polymers may find broad biomedical applications such as fluorescence-based bioimaging and tissue engineering.
“…Mainly two approaches have been utilized to incorporate fluorescent dyes into polymeric materials: physical blending [18][19][20][21] and chemical linkage. 5,22,23 Physically mixing organic dyes into polymers has advantage of attaining new properties without synthesizing new polymer structures. Fluorescence quenching induced by phase separation, however, can occur when the dye is not compatible in the polymer matrix.…”
Well-defined 1,4-diketo-3,6-di(thiophen-2-yl)pyrrolo [3,4-c]pyrrole (DTDPP) labeled polycaprolactones (PCL) with different chain lengths were synthesized and characterized. The effect of polymer chain lengths on the optical properties of DTDPP in solid states was studied by UV-Vis absorption spectroscopy as well as steady-state and dynamic fluorescence spectroscopies. Our results indicate that when the PCL side chain is extended to a certain length, the intermolecular aggregation of DTDPP units can be reduced significantly due to segregation effect of PCL. This approach offers a new facile strategy to address the common problem of aggregationcaused quenching existing in organic fluorophores. These highly fluorescent biodegradable PCL polymers may find broad biomedical applications such as fluorescence-based bioimaging and tissue engineering.
“…We use the imide functionality to link the functional naphthalimide chromophores to a norbornene residue which can be polymerized using ring-opening metathesis polymerization (ROMP). In the resulting 4-substituted 1,8-naphthalimide (formally, 6-substituted (2-alkyl)-1 H -benzo[ de ]isoquinoline-1,3(2 H )-dione) system, substituents are introduced in 6-position which can be varied and have a strong influence on the photophysical properties [28, 29].
…”
Highly fluorescent and photostable (2-alkyl)-1H-benzo[de]isoquinoline-1,3(2H)-diones with a polymerizable norbornene scaffold have been synthesized and polymerized using ring-opening metathesis polymerization. The monomers presented herein could be polymerized in a living fashion, using different comonomers and different monomer ratios. All obtained materials showed good film-forming properties and bright fluorescence caused by the incorporated push–pull chromophores. Additionally, one of the monomers containing a methylpiperazine functionality showed protonation-dependent photoinduced electron transfer which opens up interesting applications for logic gates and sensing.Graphical abstract
“…Such structures may resemble folded proteins in their organization. Recent publications (Breul et al 2013 ) demonstrate strong efforts to proceed in this direction.…”
This chapter provides comparative analysis of properties of different nanoscale materials to absorb and emit visual and near-IR light with the focus on their applications in sensing and imaging technologies. Nowadays we observe that in these applications the novel nanoscale fl uorescent materials appear in strong competition with traditional organic dyes. They demonstrate diverse photophysical behavior and allow obtaining diverse information when they are incorporated into sensor composites or form the images in biological systems. Among these nanoscale emitters are the structures formed of organic dyes or by these dyes incorporated into different types of polymers with the resulting dramatically increased brightness. Collective excitonic effects appear when the aromatic units are coupled in conjugated polymers. Nanoscale structures formed of inorganic carbon in the form of nanodiamonds, graphene and graphene oxide pieces and the so-called carbon dots joined quite recently the family of fl uorophores. Semiconductor quantum dots present a range of bright emitters covering whole visible and near-IR spectral range. Finally, the up-converting nanocrystals make possible visible emission with near-IR excitation. Here we overview the most important features of these nanoscale materials. The following Chap. 6 will be focused on functional nanocomposites that allow extending the useful properties of these basic components.
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