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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) | Viewed by 41558

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. Ashok Kakkar

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Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, QC 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

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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

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Published Papers (10 papers)

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Editorial

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4 pages, 204 KiB  
Editorial
Celebrating Todd Marder: 65th Birthday and His Contributions to Inorganic Chemistry
by Ashok Kakkar
Molecules 2021, 26(4), 776; https://doi.org/10.3390/molecules26040776 - 3 Feb 2021
Viewed by 2320
Abstract
Professor Todd B [...] Full article
(This article belongs to the 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)

Research

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24 pages, 42925 KiB  
Article
Hybrid Boron-Carbon Chemistry
by Josep M. Oliva-Enrich, Ibon Alkorta and José Elguero
Molecules 2020, 25(21), 5026; https://doi.org/10.3390/molecules25215026 - 29 Oct 2020
Cited by 5 | Viewed by 3158
Abstract
The recently proved one-to-one structural equivalence between a conjugated hydrocarbon CnHm and the corresponding borane BnHm+n is applied here to hybrid systems, where each C=C double bond in the hydrocarbon is consecutively substituted by planar [...] Read more.
The recently proved one-to-one structural equivalence between a conjugated hydrocarbon CnHm and the corresponding borane BnHm+n is applied here to hybrid systems, where each C=C double bond in the hydrocarbon is consecutively substituted by planar B(H2)B moieties from diborane(6). Quantum chemical computations with the B3LYP/cc-pVTZ method show that the structural equivalences are maintained along the substitutions, even for non-planar systems. We use as benchmark aromatic and antiaromatic (poly)cyclic conjugated hydrocarbons: cyclobutadiene, benzene, cyclooctatetraene, pentalene, benzocyclobutadiene, naphthalene and azulene. The transformation of these conjugated hydrocarbons to the corresponding boranes is analyzed from the viewpoint of geometry and electronic structure. Full article
(This article belongs to the 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)
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15 pages, 2144 KiB  
Article
A SF5 Derivative of Triphenylphosphine as an Electron-Poor Ligand Precursor for Rh and Ir Complexes
by Maria Talavera, Silke Hinze, Thomas Braun, Reik Laubenstein and Roy Herrmann
Molecules 2020, 25(17), 3977; https://doi.org/10.3390/molecules25173977 - 1 Sep 2020
Cited by 3 | Viewed by 3675
Abstract
The synthesis of the triarylphosphine, P(p-C6H4SF5)3 containing a SF5 group, has been achieved. The experimental and theoretical studies showed that P(p-C6H4SF5)3 is a weaker [...] Read more.
The synthesis of the triarylphosphine, P(p-C6H4SF5)3 containing a SF5 group, has been achieved. The experimental and theoretical studies showed that P(p-C6H4SF5)3 is a weaker σ-donor when compared with other substituted triarylphosphines, which is consistent with the electron-withdrawing effect of the SF5 moiety. The studies also revealed a moderate air stability of the phosphine. The σ-donor capabilities of P(p-C6H4SF5)3 were estimated from the phosphorus-selenium coupling constant in SeP(p-C6H4SF5)3 and by DFT calculations. The behavior of P(p-C6H4SF5)3 as ligand has been investigated by the synthesis of the iridium and rhodium complexes [MCl(COD){P(p-C6H4SF5)3}], [MCl(CO)2{P(p-C6H4SF5)3}2] (M = Ir, Rh), or [Rh(µ-Cl)(COE){P(p-C6H4SF5)3}]2, and the molecular structures of [IrCl(COD){P(p-C6H4SF5)3}] and [Rh(µ-Cl)(COE){P(p-C6H4SF5)3}]2 were determined by single X-ray diffraction. The structures revealed a slightly larger cone angle for P(p-C6H4SF5)3 when compared to other para-substituted triarylphosphines. Full article
(This article belongs to the 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)
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Graphical abstract

22 pages, 3405 KiB  
Article
Magnetic Nanoparticles Fishing for Biomarkers in Artificial Saliva
by Arpita Saha, Hamdi Ben Halima, Abhishek Saini, Juan Gallardo-Gonzalez, Nadia Zine, Clara Viñas, Abdelhamid Elaissari, Abdelhamid Errachid and Francesc Teixidor
Molecules 2020, 25(17), 3968; https://doi.org/10.3390/molecules25173968 - 31 Aug 2020
Cited by 11 | Viewed by 5592
Abstract
Magnetic nanoparticles (MNPs) were synthesized using the colloidal co-precipitation method and further coated with silica using the Stöber process. These were functionalized with carboxylic and amine functionalities for further covalent immobilization of antibodies on these MNPs. The procedure for covalent immobilization of antibodies [...] Read more.
Magnetic nanoparticles (MNPs) were synthesized using the colloidal co-precipitation method and further coated with silica using the Stöber process. These were functionalized with carboxylic and amine functionalities for further covalent immobilization of antibodies on these MNPs. The procedure for covalent immobilization of antibodies on MNPs was developed using 1-ethyl-3-(dimethylaminopropyl)carbodiimide (EDC) and N-hydroxysuccinimide (NHS). The evaluation of the efficiency of the coupling reaction was carried out by UV-vis spectrophotometry. The developed antibodies coupled to MNPs were tested for the pre-concentration of two biomarkers tumor necrosis factor alpha (TNF-α) and Interleukin-10 (IL-10). Both biomarkers were assessed in the matrix based on phosphate-buffered saline solution (PBS) and artificial saliva (AS) to carry out the demonstration of the format assay. Supernatants were used to determine the number of free biomarkers for both studies. Reduction of the nonspecific saliva protein adsorption on the surface of the complex antibodies-MNPs to levels low enough to allow the detection of biomarkers in complex media has been achieved. Full article
(This article belongs to the 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)
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11 pages, 2476 KiB  
Article
Reactions of Dihaloboranes with Electron-Rich 1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadienes
by Li Ma, Xiaolin Zhang, Wenbo Ming, Shengxin Su, Xiaoyong Chang and Qing Ye
Molecules 2020, 25(12), 2875; https://doi.org/10.3390/molecules25122875 - 22 Jun 2020
Cited by 4 | Viewed by 3353
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 3–11 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 3–11 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
(This article belongs to the 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)
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23 pages, 4789 KiB  
Article
m-Carborane as a Novel Core for Periphery-Decorated Macromolecules
by Ines Bennour, Francesc Teixidor, Zsolt Kelemen and Clara Viñas
Molecules 2020, 25(12), 2814; https://doi.org/10.3390/molecules25122814 - 18 Jun 2020
Cited by 8 | Viewed by 4545
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
(This article belongs to the 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)
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16 pages, 2887 KiB  
Article
Deboronation-Induced Ratiometric Emission Variations of Terphenyl-Based Closo-o-Carboranyl Compounds: Applications to Fluoride-Sensing
by Hyunhee So, Min Sik Mun, Mingi Kim, Jea Ho Kim, Ji Hye Lee, Hyonseok Hwang, Duk Keun An and Kang Mun Lee
Molecules 2020, 25(10), 2413; https://doi.org/10.3390/molecules25102413 - 21 May 2020
Cited by 9 | Viewed by 3288
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
(This article belongs to the 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)
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12 pages, 2102 KiB  
Article
Ruthenacarborane–Phenanthroline Derivatives as Potential Metallodrugs
by Martin Kellert, Imola Sárosi, Rajathees Rajaratnam, Eric Meggers, Peter Lönnecke and Evamarie Hey-Hawkins
Molecules 2020, 25(10), 2322; https://doi.org/10.3390/molecules25102322 - 15 May 2020
Cited by 7 | Viewed by 3587
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 2–5 are air and moisture stable under ambient conditions. They show excellent solubility in organic solvents, but low solubility in water. Full article
(This article belongs to the 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)
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Review

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22 pages, 4661 KiB  
Review
Recent Advances in π-Conjugated N^C-Chelate Organoboron Materials
by Ashanul Haque, Rayya A. Al-Balushi, Paul R. Raithby and Muhammad S. Khan
Molecules 2020, 25(11), 2645; https://doi.org/10.3390/molecules25112645 - 6 Jun 2020
Cited by 33 | Viewed by 5113
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
(This article belongs to the 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)
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18 pages, 7326 KiB  
Review
Tri(boryl)alkanes and Tri(boryl)alkenes: The Versatile Reagents
by Oriol Salvadó and Elena Fernández
Molecules 2020, 25(7), 1758; https://doi.org/10.3390/molecules25071758 - 10 Apr 2020
Cited by 29 | Viewed by 5266
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
(This article belongs to the 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)
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