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Chemical Reviews

Tamal Chatterjee, Vijayendra S Shetti, Ritambhara Sharma, Mangalampalli Ravikanth
The heteroatom-containing porphyrin analogues or core-modified porphyrins that resulted from the replacement of one or two pyrrole rings with other five-membered heterocycles such as furan, thiophene, selenophene, tellurophene, indene, phosphole, and silole are highly promising macrocycles and exhibit quite different physicochemical properties compared to regular azaporphyrins. The properties of heteroporphyrins depend on the nature and number of different heterocycle(s) present in place of pyrrole ring(s)...
November 4, 2016: Chemical Reviews
Rafał Orłowski, Dorota Gryko, Daniel T Gryko
Corroles have come a long way from being a curiosity to being a mainstream research topic. They are now regularly synthesized in numerous research laboratories worldwide with diverse specific aims in mind. In this review we present a comprehensive description of corroles' synthesis, developed both before and after 1999. To aid the investigator in developing synthetic strategies, some of the sections culminate in tables containing comparisons of various methodologies leading to meso-substituted corroles. The remaining challenges are delineated...
November 4, 2016: Chemical Reviews
Vincent Froidevaux, Claire Negrell, Sylvain Caillol, Jean-Pierre Pascault, Bernard Boutevin
Amines are key intermediates in the chemical industry due to their nucleophilic characteristic which confers a high reactivity to them. Thus, they are key monomers for the synthesis of polyamides, polyureas, polyepoxydes, which are all of growing interest in automotive, aerospace, building, or health applications. Despite a growing interest for biobased monomers and polymers, and particularly polyamides, it should be noticed that very few natural amines are available. Actually, there is only chitosan and poly(lysine)...
November 3, 2016: Chemical Reviews
Jean-Rémi Pouliot, François Grenier, J Terence Blaskovits, Serge Beaupré, Mario Leclerc
Direct (hetero)arylation polymerization (DHAP) has recently been established as an environmentally benign method for the preparation of conjugated polymers. This synthetic tool features the formation of C-C bonds between halogenated (hetero)arenes and simple (hetero)arenes with active C-H bonds, thereby circumventing the preparation of organometallic derivatives and decreasing the overall production cost of conjugated polymers. Since its inception, selectivity and reactivity of DHAP procedures have been improved tremendously through the careful scrutinity of polymerization outcomes and the fine-tuning of reaction conditions...
November 3, 2016: Chemical Reviews
Jun-Ichiro Setsune
A large number of porphyrinoids containing 2,2'-bipyrrole subunits have appeared since they were originally found as a component of sapphyrin and corrole, and it was found that the bipyrrole subunit endowed macrocycles with specific geometric features and electronic properties. Synthetic methods for bipyrrole-containing precursors for porphyrinoid are summarized in this review; these include coupling reactions of pyrrole rings, pyrrole ring-forming reactions leading directly to bipyrrole units, and synthetic reactions for oligopyrrolic compounds...
November 1, 2016: Chemical Reviews
Bryan M Hunter, Harry B Gray, Astrid M Müller
Water oxidation is a key chemical transformation for the conversion of solar energy into chemical fuels. Our review focuses on recent work on robust earth-abundant heterogeneous catalysts for the oxygen-evolving reaction (OER). We point out that improvements in the performance of OER catalysts will depend critically on the success of work aimed at understanding reaction barriers based on atomic-level mechanisms. We highlight the challenge of obtaining acid-stable OER catalysts, with proposals for elements that could be employed to reach this goal...
October 31, 2016: Chemical Reviews
Geoff P Horsman, David L Zechel
Organophosphonic acids are unique as natural products in terms of stability and mimicry. The C-P bond that defines these compounds resists hydrolytic cleavage, while the phosphonyl group is a versatile mimic of transition-states, intermediates, and primary metabolites. This versatility may explain why a variety of organisms have extensively explored the use organophosphonic acids as bioactive secondary metabolites. Several of these compounds, such as fosfomycin and bialaphos, figure prominently in human health and agriculture...
October 27, 2016: Chemical Reviews
Soji Shimizu
Subporphyrinato boron (subporphyrin) was elusive until the syntheses of tribenzosubporphine in 2006 and meso-aryl-substituted subporphyrin in 2007. These novel contracted analogues possess a 14π-electron conjugated system embedded in a bowl-shaped structure. They exhibit absorption and fluorescence in the UV/vis region and nonlinear optical properties due to their octupolar structures. The unique coordination geometry around the central boron atom in the structure of subporphyrin enabled investigation of rare boron species, such as borenium cations, boron hydrides, and boron peroxides...
October 25, 2016: Chemical Reviews
Maura Marinozzi, Fabrizio Pertusati, Michaela Serpi
The compounds characterized by the presence of a λ(5)-phosphorus functionality at the α-position with respect to the diazo moiety, here referred to as λ(5)-phosphorus-containing α-diazo compounds (PCDCs), represent a vast class of extremely versatile reagents in organic chemistry and are particularly useful in the preparation of phosphonate- and phosphinoxide-functionalized molecules. Indeed, thanks to the high reactivity of the diazo moiety, PCDCs can be induced to undergo a wide variety of chemical transformations...
October 24, 2016: Chemical Reviews
Jay A Labinger
Recent developments in C-H bond activation and functionalization by Pt complexes are surveyed. Topics include the following: fundamental mechanistic investigations of C-H activation; stoichiometric intra- and intermolecular C-H activation; reactions of dioxygen with Pt(II) complexes that may be relevant to substrate oxygenation; and both stoichiometric and catalytic formation of C-O, C-C, and C-B bonds via C-H activation. Current interests and trends are discussed, both in the context of historical work and to forecast future directions and opportunities for the field...
October 21, 2016: Chemical Reviews
Tim Stauch, Andreas Dreuw
In quantum mechanochemistry, quantum chemical methods are used to describe molecules under the influence of an external force. The calculation of geometries, energies, transition states, reaction rates, and spectroscopic properties of molecules on the force-modified potential energy surfaces is the key to gain an in-depth understanding of mechanochemical processes at the molecular level. In this review, we present recent advances in the field of quantum mechanochemistry and introduce the quantum chemical methods used to calculate the properties of molecules under an external force...
October 21, 2016: Chemical Reviews
Ruijie D Teo, Jae Youn Hwang, John Termini, Zeev Gross, Harry B Gray
Corroles are exceptionally promising platforms for the development of agents for simultaneous cancer-targeting imaging and therapy. Depending on the element chelated by the corrole, these theranostic agents may be tuned primarily for diagnostic or therapeutic function. Versatile synthetic methodologies allow for the preparation of amphipolar derivatives, which form stable noncovalent conjugates with targeting biomolecules. These conjugates can be engineered for imaging and targeting as well as therapeutic function within one theranostic assembly...
October 19, 2016: Chemical Reviews
Atanu Acharya, Alexey M Bogdanov, Bella L Grigorenko, Ksenia B Bravaya, Alexander V Nemukhin, Konstantin A Lukyanov, Anna I Krylov
Photoinduced reactions play an important role in the photocycle of fluorescent proteins from the green fluorescent protein (GFP) family. Among such processes are photoisomerization, photooxidation/photoreduction, breaking and making of covalent bonds, and excited-state proton transfer (ESPT). Many of these transformations are initiated by electron transfer (ET). The quantum yields of these processes vary significantly, from nearly 1 for ESPT to 10(-4)-10(-6) for ET. Importantly, even when quantum yields are relatively small, at the conditions of repeated illumination the overall effect is significant...
October 18, 2016: Chemical Reviews
Eiji Yashima, Naoki Ousaka, Daisuke Taura, Kouhei Shimomura, Tomoyuki Ikai, Katsuhiro Maeda
In this review, we describe the recent advances in supramolecular helical assemblies formed from chiral and achiral small molecules, oligomers (foldamers), and helical and nonhelical polymers from the viewpoints of their formations with unique chiral phenomena, such as amplification of chirality during the dynamic helically assembled processes, properties, and specific functionalities, some of which have not been observed in or achieved by biological systems. In addition, a brief historical overview of the helical assemblies of small molecules and remarkable progress in the synthesis of single-stranded and multistranded helical foldamers and polymers, their properties, structures, and functions, mainly since 2009, will also be described...
October 18, 2016: Chemical Reviews
Javier Miró, Carlos Del Pozo
No abstract text is available yet for this article.
October 18, 2016: Chemical Reviews
Atanu Jana, Masatoshi Ishida, Jung Su Park, Steffen Bähring, Jan O Jeppesen, Jonathan L Sessler
After the epochal discovery of the "organic metal", namely, tetrathiafulvalene (TTF)-7,7,8,8-tetracyano-p-quinodimethane (TCNQ) dyad in 1973, scientists have made efforts to derivatize TTF for constructing various supramolecular architectures to control the charge-transfer processes by adjusting the donor-acceptor strength of the dyads for numerous applications. The interesting inherent electronic donor properties of TTFs control the overall electrochemical properties of the supramolecular structures, leading to the construction of highly efficient optoelectronic materials, photovoltaic solar cells, organic field-effect transistors, and optical sensors...
October 18, 2016: Chemical Reviews
Ivano Alessandri, John R Lombardi
Dielectrics represent a new frontier for surface-enhanced Raman scattering. They can serve as either a complement or an alternative to conventional, metal-based SERS, offering key advantages in terms of low invasiveness, reproducibility, versatility, and recyclability. In comparison to metals, dielectric systems and, in particular, semiconductors are characterized by a much greater variety of parameters and properties that can be tailored to achieve enhanced Raman scattering or related effects. Light-trapping and subwavelength-focusing capabilities, morphology-dependent resonances, control of band gap and stoichiometry, size-dependent plasmons and excitons, and charge transfer from semiconductors to molecules and vice versa are a few examples of the manifold opportunities associated with the use of semiconductors as SERS-active materials...
October 14, 2016: Chemical Reviews
Ewa D Raczyńska, Jean-François Gal, Pierre-Charles Maria
Nitrogen bases containing one or more pushing amino-group(s) directly linked to a pulling cyano, imino, or phosphoimino group, as well as those in which the pushing and pulling moieties are separated by a conjugated spacer (C═X)n, where X is CH or N, display an exceptionally strong basicity. The n-π conjugation between the pushing and pulling groups in such systems lowers the basicity of the pushing amino-group(s) and increases the basicity of the pulling cyano, imino, or phosphoimino group. In the gas phase, most of the so-called push-pull nitrogen bases exhibit a very high basicity...
October 14, 2016: Chemical Reviews
David Polcari, Philippe Dauphin-Ducharme, Janine Mauzeroll
Scanning electrochemical microscopy (SECM) is an electroanalytical scanning probe technique capable of imaging substrate topography and local reactivity with high resolution. Since its inception in 1989, it has expanded into a wide variety of research areas including biology, corrosion, energy, kinetics, instrumental development, and surface modification. In the past 25 years, over 1800 peer-reviewed publications have focused on SECM, including several topical reviews. However, these reviews often omit key details, forcing readers to search the literature...
October 13, 2016: Chemical Reviews
Oksana Ostroverkhova
Organic (opto)electronic materials have received considerable attention due to their applications in thin-film-transistors, light-emitting diodes, solar cells, sensors, photorefractive devices, and many others. The technological promises include low cost of these materials and the possibility of their room-temperature deposition from solution on large-area and/or flexible substrates. The article reviews the current understanding of the physical mechanisms that determine the (opto)electronic properties of high-performance organic materials...
October 10, 2016: Chemical Reviews
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