Fluorescent Molecular Rotors for Viscosity Sensors

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Abstract

Fluorescent molecular rotors (FMRs) can act as viscosity sensors in various media including subcellular organelles and microfluidic channels. In FMRs, the rotation of rotators connected to a fluorescent π-conjugated bridge is suppressed by increasing environmental viscosity, resulting in increasing fluorescence (FL) intensity. In this minireview, we describe recently developed FMRs including push-pull type π-conjugated chromophores, meso-phenyl (borondipyrromethene) (BODIPY) derivatives, dioxaborine derivatives, cyanine derivatives, and porphyrin derivatives whose FL mechanism is viscosity-responsive. In addition, FMR design strategies for addressing various issues (e.g., obtaining high FL contrast, internal FL references, and FL intensity-contrast trade-off) and their biological and microfluidic applications are also discussed.

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AIE macromolecules: syntheses, structures and functionalities.

RONGRONG HU, Nelson Leung, Ben Tang (2014)

Macromolecules with aggregation-induced emission (AIE) attributes are a class of luminescent materials that display enhanced emission when they are aggregated. They have attracted much attention because of their good solubility, processability, high emission efficiency in the aggregated states, etc. A large variety of AIE macromolecules have been developed, showing exponential growth of research interest in this field. This review summarizes the design principles and recent synthetic advancements, topological structures, as well as the frontiers of functionalities and potential applications of AIE macromolecules, especially fluorescence sensing, biological applications and optoelectronic applications, with an emphasis on the recent progress. New luminogenic systems without conventional chromophores displaying aggregated state emission are discussed. The highly dense clusters of heteroatoms with lone pair electrons in these systems may serve as the chromophore and are cited as "heterodox clusters". It is expected that the mechanistic insights into the AIE phenomena, based on the restriction of intramolecular motions and structure rigidification, can guide the future design of AIE materials with fascinating structures and functionalities.

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Recent advances in twisted intramolecular charge transfer (TICT) fluorescence and related phenomena in materials chemistry

Gen-ichi Konishi, Shunsuke Sasaki, Gregor P. C. Drummen (2016)

Twisted intramolecular charge transfer (TICT) is an electron transfer process that occurs upon photoexcitation in molecules that usually consist of a donor and acceptor part linked by a single bond. Twisted intramolecular charge transfer (TICT) is an electron transfer process that occurs upon photoexcitation in molecules that usually consist of a donor and acceptor part linked by a single bond. Following intramolecular twisting, the TICT state returns to the ground state either through red-shifted emission or by nonradiative relaxation. The emission properties are potentially environment-dependent, which makes TICT-based fluorophores ideal sensors for solvents, (micro)viscosity, and chemical species. Recently, several TICT-based materials have been discovered to become fluorescent upon aggregation. Furthermore, various recent studies in organic optoelectronics, non-linear optics and solar energy conversions utilised the concept of TICT to modulate the electronic-state mixing and coupling on charge transfer states. This review presents a compact overview of the latest developments in TICT research, from a materials chemistry point of view.

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Imaging intracellular viscosity of a single cell during photoinduced cell death.

Milan Balaz, Klaus Suhling, Peter Ogilby … (2009)

Diffusion-mediated cellular processes, such as metabolism, signalling and transport, depend on the hydrodynamic properties of the intracellular matrix. Photodynamic therapy, used in the treatment of cancer, relies on the generation of short-lived cytotoxic agents within a cell on irradiation of a drug. The efficacy of this treatment depends on the viscosity of the medium through which the cytotoxic agent must diffuse. Here, spectrally resolved fluorescence measurements of a porphyrin-dimer-based molecular rotor are used to quantify intracellular viscosity changes in single cells. We show that there is a dramatic increase in the viscosity of the immediate environment of the rotor on photoinduced cell death. The effect of this viscosity increase is observed directly in the diffusion-dependent kinetics of the photosensitized formation and decay of a key cytotoxic agent, singlet molecular oxygen. Using these tools, we provide insight into the dynamics of diffusion in cells, which is pertinent to drug delivery, cell signalling and intracellular mass transport.