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Principles Of Fluorescence Spectroscopy

The successful isolation and characterization of an N-heterocyclic carbene in 1991 opened up a new class of organic compounds for investigation. From these beginnings as academic curiosities, N-heterocyclic carbenes today rank among the most powerful tools in organic chemistry, with numerous applications in commercially important processes. Here we provide a concise overview of N-heterocyclic carbenes in modern chemistry, summarizing their general properties and uses and highlighting how these features are being exploited in a selection of pioneering recent studies.

An overview of N-heterocyclic carbenes

Organic reactions that involve the direct functionalization of non-activated C–H bonds represent an attractive class of transformations which maximize atom- and step-economy, and simplify chemical synthesis. Due to the high stability of C–H bonds, these processes, however, have most often required harsh reaction conditions, which has drastically limited their use as tools for the synthesis of complex organic molecules. Following the increased understanding of mechanistic aspects of C–H activation gained over recent years, great strides have been taken to design and develop new protocols that proceed efficiently under mild conditions and duly benefit from improved functional group tolerance and selectivity. In this review, we present the current state of the art in this field and detail C–H activation transformations reported since 2011 that proceed either at or below ambient temperature, in the absence of strongly acidic or basic additives or without strong oxidants. Furthermore, by identifying and discussing the major strategies that have led to these improvements, we hope that this review will serve as a useful conceptual overview and inspire the next generation of mild C–H transformations.

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Mild metal-catalyzed C–H activation: examples and concepts

Supramolecular Chirality in Self-Assembled Systems

Fluorine has received great attention in all fields of science. “Small atom with a big ego” was the title of the Symposium at the ACS meeting in San Francisco in 2000, where a number of the current scientific and industrial aspects of fluorine chemistry made possible by the small size and high electronegativity of the atom were discussed. This small atom has provided mankind with significant benefits in special products such as poly(tetrafluroethylene) (PTFE), freon, fluoro-liquid crystals, optical fiber, pharmaceutical and agrochemical compounds, and so on, all of which have their own unique properties that are otherwise difficult to obtain.1 For instance, at present, up to 30% of agrochemicals and 10% of pharmaceuticals currently used contain fluorine atoms. Therefore, organic fluorine compounds have received a great deal of interest and attention from the scientists involved in diverse fields of science and technology. Now, not only C-F bond formation but also selective C-F bond activation have become current subjects of active investigation from the viewpoint of effective synthesis of fluoroorganic compounds. The former is highlighted by designing a sophisticated fluorinating reagent for regioand stereocontrolled fluorination and developing versatile multifunctional and easily prepared building blocks. C-F bond formation has been treated extensively in several reviews2 and books.3 The latter is a subject that has been less explored but would be promising for selective defluorination of aliphatic fluorides, cross-coupling with aryl fluorides, and * To whom correspondence should be addressed. Phone: 81-78-803-5799. Fax: 81-78-803-5799. E-mail: amii@kobe-u.ac.jp and uneyamak@cc.okayamau.ac.jp. † Kobe University. ‡ Okayama University. Chem. Rev. 2009, 109, 2119–2183 2119

C-F bond activation in organic synthesis.

An organic field effect transistor featuring the chiral molecule helicene acts as a photodetector that is able to distinguish between left- and right-handed circularly polarized light.

Circularly polarized light detection by a chiral organic semiconductor transistor

SIRT proteins play an important role in the survival and drug resistance of tumor cells, especially during chemotherapy. In this study, we investigated the potency, specificity, and cellular targets of three SIRT inhibitors, Sirtinol, Salermide, and EX527. Cell proliferative and cell cycle analyses showed that Sirtinol and Salermide, but not EX527, were effective in inducing cell death at concentrations of 50 μmol/L or over in MCF-7 cells. Instead, EX527 caused cell cycle arrest at G1 at comparable concentrations. In vitro SIRTassays using a p53 peptide substrate showed that all three compounds are potent SIRT1/2 inhibitors, with EX527 having the highest inhibitory activity for SIRT1. Computational docking analysis showed that Sirtinol and Salermide have high degrees of selectivity for SIRT1/2, whereas EX527 has high specificity for SIRT1 but not SIRT2. Consistently, Sirtinol and Salermide, but not EX527, treatment resulted in the in vivo acetylation of the SIRT1/2 target p53 and SIRT2 target tubulin in MCF-7 cells, suggesting that EX527 is ineffective in inhibiting SIRT2 and that p53 mediates the cytotoxic function of Sirtinol and Salermide. Studies using breast carcinoma cell lines and p53-deficient mouse fibroblasts confirmed that p53 is essential for the Sirtinol and Salermideinduced apoptosis. Further, we showed using small interfering RNA that silencing both SIRTs, but not SIRT1 and SIRT2 individually, can induce cell death in MCF-7 cells. Together, our results identify the specificity and cellular targets of these novel inhibitors and suggest that SIRT inhibitors require combined targeting of both SIRT1 and SIRT2 to induce p53 acetylation and cell death. Mol Cancer Ther; 9(4); 844–55. ©2010 AACR.

https://mct.aacrjournals.org/content/molcanther/9/4/844.full.pdf

SIRT Inhibitors Induce Cell Death and p53 Acetylation through Targeting Both SIRT1 and SIRT2

Chirality is a fundamental symmetry property; chiral objects, such as chiral small molecules, exist as a pair of non-superimposable mirror images. Although small-molecule chirality is routinely considered in biologically focused application areas (such as drug discovery and chemical biology), other areas of scientific development have not considered small-molecule chirality to be central to their approach. In this Review, we highlight recent research in which chirality has enabled advancement in technological applications. We showcase examples in which the presence of small-molecule chirality is exploited in ways beyond the simple interaction of two different chiral molecules; this can enable the detection and emission of chiral light, help to control molecular motion, or provide a means to control electron spin and bulk charge transport. Thus, we demonstrate that small-molecule chirality is a highly promising avenue for a wide range of technologically oriented scientific endeavours. Although it is a fundamental property of many small molecules, chirality is not widely exploited in materials applications as its benefits are not widely recognized — indeed, the need for stereoselective synthesis may be seen as a disadvantage. In this Review, we highlight recent research in which chirality has had an enabling impact in technological applications.

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The added value of small-molecule chirality in technological applications

Organic light-emitting diodes (OLEDs) are devices that utilize an emissive electroluminescent organic semiconductor (OSC) thin film sandwiched between two electrodes. Employing polymers as the OSC is a highly attractive approach due to their easy solution processibility. This results in low cost, large area device fabrication possibilities using printing techniques. Circularly polarized (CP) light is central to a large range of current and future display and photonic technologies, including highly efficient LCD backlights,1 optical quantum information processing and communication,2, 3 and optical spintronics.4 There is therefore high interest in constructing CP-light-emitting devices. Whilst the use of wide-band reflective polarizers as passive components in polymer LED (PLED) devices is one means to engineer a CP light output, this results in a relatively complex and thick device architecture, requiring an additional liquid-crystal cell.5 The direct generation of CP light from a conventional PLED would be far more favorable in terms of simplicity, compactness, energy efficiency and product cost, and thus there has been significant interest in their development.

/pdf/induction-of-circularly-polarized-electroluminescence-from-2zyb6ms8j3.pdf

Induction of Circularly Polarized Electroluminescence from an Achiral Light-Emitting Polymer via a Chiral Small-Molecule Dopant

Circularly polarized (CP) light is of interest in areas such as quantum optical computing, optical spintronics, biomedicine, and high efficiency displays. Direct emission of CP light from organic light-emitting diodes (OLEDs) has been a focus of research as it has the immediate application of increasing efficiency and simplifying device architecture in OLED based displays. High dissymmetry (gEL) factor values have been reported for devices employing fluorescent polymers, but these CP-OLEDs are limited in their ultimate efficiencies by the type of emissive electronic transitions involved. In contrast, phosphorescent OLEDs (PHOLEDs) can emit light from triplet excited states and can therefore achieve very high efficiencies. However, CP-PHOLEDs are significantly understudied, and the two previous reports suffered from very low brightness or gEL values. Here, we use a platinahelicene complex to construct a CP-PHOLED that achieves both a display level brightness and a high gEL factor. The dissymmetry of CP emi...

http://pubs.acs.org/doi/pdf/10.1021/jacs.6b02463

Matthew J. Fuchter

Papers

Circularly polarized light detection by a chiral organic semiconductor transistor

SIRT Inhibitors Induce Cell Death and p53 Acetylation through Targeting Both SIRT1 and SIRT2

The added value of small-molecule chirality in technological applications

Induction of Circularly Polarized Electroluminescence from an Achiral Light-Emitting Polymer via a Chiral Small-Molecule Dopant

Circularly Polarized Phosphorescent Electroluminescence with a High Dissymmetry Factor from PHOLEDs Based on a Platinahelicene.