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Special Issue "Boron in Catalysis and Materials Chemistry: A Themed Issue in Honor of Professor Todd B. Marder on the Occasion of His 65th Birthday"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organometallic Chemistry".

Deadline for manuscript submissions: closed (1 June 2020).

Special Issue Editor

Prof. Dr. Ashok Kakkar
Website
Guest Editor
Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec, H3A 0B8, Canada
Interests: nanostructures; soft nanoparticles; macromolecules; dendrimers; miktoarm polymers; telodendrimers, naked nanocarriers; metal nanoparticles; gold nanoshells; iron oxide nanoparticles; nanomedicine; drug delivery; diagnostics
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Special Issue Information

Dear Colleagues,

Dr. Todd B Marder is an eminent inorganic chemist who has made key contributions to the areas of metal-boron and organometallic chemistry. His fundamental research has led to applications in a diverse range of areas including homogeneous catalysis, nonlinear optics, crystal engineering, as well as small molecule triggers of stem cell differentiation. He has been a great promoter of collaborative academic efforts to resolve key problems in science. Dr. Todd Marder is currently a Professor and Chair of Inorganic Chemistry at the institute of inorganic chemistry, Julius-Maximilians-Universitat, Wurzburg, Germay. He received his undergraduate training in science (BSc, 1976) at the Masschusetts Institute of Technology, and his graduate studies (PhD, 1981) at the University of California under the direction of Professor Fred Hawthorne. He completed his post-doctoral studies in the laboratory of Professor FGA Stone at the University of Bristol (UK). After a short stint at DuPont in Wilmington, Delaware (USA), he began his academic career at the University of Waterloo (Canada) in 1985, and was quickly promoted to full professor in 1993. He subsequently moved to University of Durham in England in 1997 as Chair of Inorganic Chemistry, which he held until 2012. He then took up the position of Professor and Chair of Inorganic Chemistry in 2012 at the Institut für Anorganische Chemie, Universität Würzburg, Germany.

Professor Marder has received several awards including the Rutherford Memorial Medal for Chemistry (1995); the Royal Society of Chemistry Award in Main Group Element Chemistry for his contributions to the chemistry of boron and its organometallic compounds, and to their applications in the development of catalysts and chromophores (2008); JSPS Invitation Fellowship by the Japan Society for the Promotion of Science (2010); Humboldt Research Award by the Alexander von Humboldt Foundation in Germany (2010); Wolfson Research Merit Award by the Royal Society, UK (2010); and the Royal Society of Chemistry Award in Organometallic Chemistry (2015). He has held several Visiting Professorships worldwide, and has served on the editorial boards of several high impact journals. He has a high h-index and his publications are among some of the highly cited.

“Molecules” is highly pleased to host a Special Issue, and invites scientists to submit original contributions to “Boron in Catalysis and Materials Chemistry: A Themed Issue in Honor of Professor Todd B. Marder on the Occasion of His 65th Birthday.

Prof. Dr. Ashok Kakkar
Guest Editor

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2000 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Boron compounds
  • Diboranes
  • Metal-boron compounds
  • B-H Activation
  • Organometallic chemistry
  • Homogeneous catalysis
  • Boron in cross-coupling reactions
  • Borylation
  • Carbon-boron coupling
  • Catechol-, Pinacol-, and Neopentaneglycolborane
  • Fluorescence agents
  • Chromophores
  • Imaging
  • Luminescent organometallics
  • Nonlinear optics
  • Crystal Engineering
  • Synthetic Retinoids
  • Boron in biology

Published Papers (6 papers)

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Research

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Open AccessArticle
Reactions of Dihaloboranes with Electron-Rich 1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadienes
Molecules 2020, 25(12), 2875; https://doi.org/10.3390/molecules25122875 - 22 Jun 2020
Abstract
The reactions of electron-rich organosilicon compounds 1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadiene (1), 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadiene (2), and 1,1′-bis(trimethylsilyl)-1,1′-dihydro-4,4′-bipyridine (12) with B-amino and B-aryl dihaloboranes afforded a series of novel B=N-bond-containing compounds 311 and 13. The B=N rotational barriers [...] Read more.
The reactions of electron-rich organosilicon compounds 1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadiene (1), 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadiene (2), and 1,1′-bis(trimethylsilyl)-1,1′-dihydro-4,4′-bipyridine (12) with B-amino and B-aryl dihaloboranes afforded a series of novel B=N-bond-containing compounds 311 and 13. The B=N rotational barriers of 7 (>71.56 kJ/mol), 10 (58.79 kJ/mol), and 13 (58.65 kJ/mol) were determined by variable-temperature 1H-NMR spectroscopy, thus reflecting different degrees of B=N double bond character in the corresponding compounds. In addition, ring external olefin isomers 11 were obtained by a reaction between 2 and DurBBr2. All obtained B=N-containing products were characterized by multinuclear NMR spectroscopy. Compounds 5, 9, 10a, 11, and 13a were also characterized by single-crystal X-ray diffraction analysis. Full article
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Open AccessFeature PaperArticle
m-Carborane as a Novel Core for Periphery-Decorated Macromolecules
Molecules 2020, 25(12), 2814; https://doi.org/10.3390/molecules25122814 - 18 Jun 2020
Abstract
Closo m-C2B10H12 can perform as a novel core of globular periphery-decorated macromolecules. To do this, a new class of di and tetrabranched m-carborane derivatives has been synthesized by a judicious choice of the synthetic procedure, starting [...] Read more.
Closo m-C2B10H12 can perform as a novel core of globular periphery-decorated macromolecules. To do this, a new class of di and tetrabranched m-carborane derivatives has been synthesized by a judicious choice of the synthetic procedure, starting with 9,10-I2-1,7-closo-C2B10H10. The 2a-NPA (sum of the natural charges of the two bonded atoms) value for a bond, which is defined as the sum of the NPA charges of the two bonded atoms, matches the order of electrophilic reaction at the different cluster bonds of the icosahedral o-and m- carboranes that lead to the formation of B-I bonds. As for m-carborane, most of the 2a-NPA values of B-H vertexes are positive, and their functionalization is more challenging. The synthesis and full characterization of dibranched 9,10-R2-1,7-closo-carborane (R = CH2CHCH2, HO(CH2)3, Cl(CH2)3, TsO(CH2)3, C6H5COO(CH2)3, C6H5COO(CH2)3, N3(CH2)3, CH3CHCH, and C6H5C2N3(CH2)3) compounds as well as the tetrabranched 9,10-R2-1,7-R2-closo-C2B10H8 (R = CH2CHCH2, HO(CH2)3) are presented. The X-ray diffraction of 9,10-(HO(CH2)3)2-1,7-closo-C2B10H10 and 9,10-(CH3CHCH)2-1,7-closo-C2B10H10, as well as their Hirshfeld surface analysis and decomposed fingerprint plots, are described. These new reported tetrabranched m-carborane derivatives provide a sort of novel core for the synthesis of 3D radially grown periphery-decorated macromolecules that are different to the 2D radially grown core of the tetrabranched o-carborane framework. Full article
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Open AccessArticle
Deboronation-Induced Ratiometric Emission Variations of Terphenyl-Based Closo-o-Carboranyl Compounds: Applications to Fluoride-Sensing
Molecules 2020, 25(10), 2413; https://doi.org/10.3390/molecules25102413 - 21 May 2020
Abstract
Closo-o-carboranyl compounds bearing the ortho-type perfectly distorted or planar terphenyl rings (closo-DT and closo-PT, respectively) and their nido-derivatives (nido-DT and nido-PT, respectively) were synthesized and fully [...] Read more.
Closo-o-carboranyl compounds bearing the ortho-type perfectly distorted or planar terphenyl rings (closo-DT and closo-PT, respectively) and their nido-derivatives (nido-DT and nido-PT, respectively) were synthesized and fully characterized using multinuclear NMR spectroscopy and elemental analysis. Although the emission spectra of both closo-compounds exhibited intriguing emission patterns in solution at 298 and 77 K, in the film state, closo-DT mainly exhibited a π-π* local excitation (LE)-based emission in the high-energy region, whereas closo-PT produced an intense emission in the low-energy region corresponding to an intramolecular charge transfer (ICT) transition. In particular, the positive solvatochromic effect of closo-PT and theoretical calculation results at the first excited (S1) optimized structure of both closo-compounds strongly suggest that these dual-emissive bands at the high- and low-energy can be assigned to each π-π* LE and ICT transition. Interestingly, both the nido-compounds, nido-DT and nido-PT, exhibited the only LE-based emission in solution at 298 K due to the anionic character of the nido-o-carborane cages, which cannot cause the ICT transitions. The specific emissive features of nido-compounds indicate that the emissive color of closo-PT in solution at 298 K is completely different from that of nido-PT. As a result, the deboronation of closo-PT upon exposure to increasing concentrations of fluoride anion exhibits a dramatic ratiometric color change from orange to deep blue via turn-off of the ICT-based emission. Consequently, the color change response of the luminescence by the alternation of the intrinsic electronic transitions via deboronation as well as the structural feature of terphenyl rings indicates the potential of the developed closo-o-carboranyl compounds that exhibit the intense ICT-based emission, as naked-eye-detectable chemodosimeters for fluoride ion sensing. Full article
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Open AccessArticle
Ruthenacarborane–Phenanthroline Derivatives as Potential Metallodrugs
Molecules 2020, 25(10), 2322; https://doi.org/10.3390/molecules25102322 - 15 May 2020
Abstract
Ruthenium-based complexes have received much interest as potential metallodrugs. In this work, four RuII complexes bearing a dicarbollide moiety, a carbonyl ligand, and a phenanthroline-based ligand were synthesized and characterized, including single crystal diffraction analysis of compounds 2, 4, and [...] Read more.
Ruthenium-based complexes have received much interest as potential metallodrugs. In this work, four RuII complexes bearing a dicarbollide moiety, a carbonyl ligand, and a phenanthroline-based ligand were synthesized and characterized, including single crystal diffraction analysis of compounds 2, 4, and 5 and an observed side product SP1. Complexes 25 are air and moisture stable under ambient conditions. They show excellent solubility in organic solvents, but low solubility in water. Full article
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Review

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Open AccessReview
Recent Advances in π-Conjugated N^C-Chelate Organoboron Materials
Molecules 2020, 25(11), 2645; https://doi.org/10.3390/molecules25112645 - 06 Jun 2020
Abstract
Boron-containing π-conjugated materials are archetypical candidates for a variety of molecular scale applications. The incorporation of boron into the π-conjugated frameworks significantly modifies the nature of the parent π-conjugated systems. Several novel boron-bridged π-conjugated materials with intriguing structural, photo-physical and electrochemical properties have [...] Read more.
Boron-containing π-conjugated materials are archetypical candidates for a variety of molecular scale applications. The incorporation of boron into the π-conjugated frameworks significantly modifies the nature of the parent π-conjugated systems. Several novel boron-bridged π-conjugated materials with intriguing structural, photo-physical and electrochemical properties have been reported over the last few years. In this paper, we review the properties and multi-dimensional applications of the boron-bridged fused-ring π-conjugated systems. We critically highlight the properties of π-conjugated N^C-chelate organoboron materials. This is followed by a discussion on the potential applications of the new materials in opto-electronics (O-E) and other areas. Finally, attempts will be made to predict the future direction/outlook for this class of materials. Full article
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Open AccessReview
Tri(boryl)alkanes and Tri(boryl)alkenes: The Versatile Reagents
Molecules 2020, 25(7), 1758; https://doi.org/10.3390/molecules25071758 - 10 Apr 2020
Abstract
The interest of organoboron chemistry in organic synthesis is growing, together with the development of new and versatile polyborated reagents. Here, the preparation of 1,1,1-tri(boryl)alkanes, 1,2,3-tri(boryl)alkanes, 1,1,2-tri(boryl)alkanes, as well as 1,1,2-tri(boryl)alkenes as suitable and accessible polyborated systems is demonstrated as being easily applied [...] Read more.
The interest of organoboron chemistry in organic synthesis is growing, together with the development of new and versatile polyborated reagents. Here, the preparation of 1,1,1-tri(boryl)alkanes, 1,2,3-tri(boryl)alkanes, 1,1,2-tri(boryl)alkanes, as well as 1,1,2-tri(boryl)alkenes as suitable and accessible polyborated systems is demonstrated as being easily applied in the construction of new carbon-carbon and carbon-heteroatom bonds. Synthetic procedures and limitations have been collected to demonstrate the powerful strategies to construct selective molecules, taking advantages of the easy transformation of carbon-boron bond in multiple functionalities, under the total control of chemo- and stereoselectivity. Full article
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