A5025634481- Synthesis and Properties of Aromatic Compounds
- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Machine Learning in Materials Science
- Crystallography and molecular interactions
- Fullerene Chemistry and Applications
- Computational Drug Discovery Methods
- Photochromic and Fluorescence Chemistry
- Organic Electronics and Photovoltaics
- Advanced NMR Techniques and Applications
- Various Chemistry Research Topics
- Perovskite Materials and Applications
- Analytical Chemistry and Chromatography
- Advanced Chemical Physics Studies
- Porphyrin and Phthalocyanine Chemistry
- History and advancements in chemistry
- Solid-state spectroscopy and crystallography
- Chemistry and Chemical Engineering
- Graph theory and applications
- Axial and Atropisomeric Chirality Synthesis
- Conducting polymers and applications
- Photoreceptor and optogenetics research
- Asymmetric Hydrogenation and Catalysis
- Luminescence and Fluorescent Materials
- Chemical Reaction Mechanisms
Technion – Israel Institute of Technology
2012-2025
ETH Zurich
2017-2024
Board of the Swiss Federal Institutes of Technology
2017-2020
University of Haifa
2020
Scripps Research Institute
2009
Israel Institute
2009
Abstract Nucleus‐independent chemical shift (NICS)‐based methods are very popular for the determination of induced magnetic field under an external field. These used mostly (but not only) aromaticity and antiaromaticity molecules ions, both qualitatively quantitatively. The ghost atom that serves as NICS probe senses reports it in form NMR shift. However, source cannot be determined by NICS. Thus, a multi‐ring system may contain more than one current circuit (and therefore field) value...
There has been an ongoing effort to overcome the limitations associated with stability of hybrid organic-inorganic perovskite solar cells by using different organic agents as additives formulations. The functionality predominantly limited exploiting hydrogen-bonding interactions, while relevant atomic-level binding modes remain elusive. Herein, we introduce a bifunctional supramolecular modulator, 1,2,4,5-tetrafluoro-3,6-diiodobenzene, which interacts surface triple-cation double-halide...
The use of layered perovskites is an important strategy to improve the stability hybrid perovskite materials and their optoelectronic devices. However, tailoring properties requires accurate structure determination at atomic scale, which a challenge for conventional diffraction-based techniques. We demonstrate nuclear magnetic resonance (NMR) crystallography in determining mixed-spacer model composed 2-phenylethylammonium (PEA+) 2-(perfluorophenyl)ethylammonium (FEA+) moieties, revealing...
Despite impressive advances in the construction of metal–organic frameworks (MOFs), formation networks from peptidic ligands is difficult, though they are sought after for their modularity and biocompatibility. Herein we present a peptide–metal framework that consists helical oligoproline Zn/K (or Zn/Rb). The crystalline network contains pleated nanosheets with metal ions aligned strings. This unprecedented architecture derives under-appreciated London dispersion interactions between play...
Aromaticity is a fundamental concept in chemistry, underpinning the properties and reactivity of many organic compounds materials. The ability to easily accurately discern aromatic behavior key leveraging it as design element, yet most aromaticity metrics struggle combine accurate quantitative evaluation, intuitive interpretability, user-friendliness. We introduce new method, NICS2BC, which uses simple inexpensive NICS calculations generate information-rich easily-interpreted bond-current...
The aromaticity of oligomers predicts their HOMO–LUMO gaps and ionization potentials.
Abstract Incorporation of a five‐membered ring into helicene framework disrupts aromatic conjugation and provides site for selective deprotonation. The deprotonation creates an anionic cyclopentadienyl unit, switches on conjugation, leads to >200 nm red‐shift in the absorbance spectrum injects charge helical conjugated π‐system without injecting spin. Structural consequences were revealed via analysis monoanionic co‐crystallized with {K + (18‐crown‐6)(THF)} {Cs 2 (18‐crown‐6) 3 }....
We describe reductive dehydrogenative cyclizations that form hepta-, nona-, and decacyclic anionic graphene subunits from mono- bis-helicenes with an embedded five-membered ring. The reaction of can either proceed to the full double annulation or be interrupted by addition molecular oxygen at intermediate stage. regioselectivity cyclization cascade for confirms relief antiaromaticity is a dominant force these facile ring closures. Computational analysis reveals unique role preexisting...
Chemical databases are an essential tool for data-driven investigation of structure–property relationships and the design novel functional compounds. We introduce first phase COMPAS Project─a COMputational database Polycyclic Aromatic Systems. In this phase, we developed two data sets containing optimized ground-state structures a selection molecular properties ∼34k ∼9k cata-condensed polybenzenoid hydrocarbons (at GFN2-xTB B3LYP-D3BJ/def2-SVP levels, respectively) placed them in public...
In this work, interpretable deep learning was used to identify structure-property relationships governing the HOMO-LUMO gap and relative stability of polybenzenoid hydrocarbons (PBHs) using a ring-based graph representation. This representation combined with subunit-based perception PBHs, allowing chemical insights be presented in terms intuitive simple structural motifs. The resulting agree conventional organic chemistry knowledge electronic structure-based analyses also reveal new...
Polycyclic aromatic systems are highly important to numerous applications, in particular organic electronics and optoelectronics. High-throughput screening generative models that can help identify new molecules advance these technologies require large amounts of high-quality data, which is expensive generate. In this report, we present the largest freely available dataset geometries properties cata-condensed poly(hetero)cyclic calculated date. Our contains ~500k comprising 11 types...
We introduce the third installment of COMPAS Project - a COMputational database Polycyclic Aromatic Systems, focused on
Pentalenes are formally eight-π-electron antiaromatic, but π-expanded pentalenes can display varying levels of paratropicity depending on the choice annelated (hetero)arenes and geometry π-expansion (i.e., linear vs bent topologies) around [4n] core. Here, we explain effects annelation by relating electronic structure to a pair conjoined pentafulvenes.
We investigate the locality of magnetic response in polycyclic aromatic molecules using a novel deep-learning approach. Our method employs graph neural networks (GNNs) with graph-of-rings representation to predict Nucleus-Independent Chemical Shifts space around molecule. train series models, each time reducing size largest used training. The accuracy prediction remains high (MAE < 0.5 ppm), even when training model only on up 4 rings, thus providing strong evidence for response. To...
Abstract The two‐fold reduction of tetrabenzo[ a , c e g ]cyclooctatetraene (TBCOT, or tetraphenylene, 1 ) with K, Rb, and Cs metals reveals distinctive core transformation pathway: newly formed C−C bond converts the central eight‐membered ring into twisted two fused five‐membered rings. This 1.589(3)–1.606(6) Å falls single σ‐bond range generates perpendicular π‐surfaces dihedral angles 110.3(9)°–117.4(1)° in TR 2− dianions. As result, highly contorted ligand exhibits “butterfly” shape...
Abstract Polybenzenoid hydrocarbons (PBHs) are widely studied for their semiconductive properties and potential applications in organic electronics photochemistry. Understanding behavior excited states is crucial optimizing performance these applications. Here, we computationally investigate a dataset of 43 unbranched cata-condensed PBHs first singlet state (S₁), revealing clear correlations between molecular structure electronic properties. By analyzing molecules through annulation...
The Michael addition of unactivated nitriles to α,β‐unsaturated ketones is a challenging yet desirable strategy for installing alkyl cyano‐groups (R‐CN) in organic molecules. However, despite formidable efforts, using acetonitrile as donor these reactions has remained significant challenge. Herein, we report highly active manganese(I) complex [(PCNHCP)Mn(CO)2H] (1), which chemoselectively catalyzes the 1,4‐addition (incl. acetonitrile) ketones. developed methodology operates under mild...
The Michael addition of unactivated nitriles to α,β‐unsaturated ketones is a challenging yet desirable strategy for installing alkyl cyano‐groups (R‐CN) in organic molecules. However, despite formidable efforts, using acetonitrile as donor these reactions has remained significant challenge. Herein, we report highly active manganese(I) complex [(PCNHCP)Mn(CO)2H] (1), which chemoselectively catalyzes the 1,4‐addition (incl. acetonitrile) ketones. developed methodology operates under mild...
Incorporation of a BN pair into polycyclic aro- matic hydrocarbons is common approach for modulating their electronic properties. However, conceptual and quantitative framework rationalizing the observed effects has not been developed, general structure-property relationships remain elusive. In this work, we perform data-driven investigation that leads to concrete principles rational design (BN)1-PBHs with targeted We construct new chemical database, COMPAS-4, which contains geometries...
ABSTRACT Polybenzenoid hydrocarbons (PBHs) are widely studied for their semiconductive properties and potential applications in organic electronics photochemistry. Understanding behavior excited states is crucial optimizing performance these applications. Here, we computationally investigate a dataset of 43 unbranched cata ‐condensed PBHs first singlet state (S₁), revealing clear correlations between molecular structure electronic properties. By analyzing molecules through annulation...
Aromatic compounds are prevalent in both nature and man-made materials, yet their properties still not fully understood therefore hard to predict. Herein, we introduce an additivity scheme for the prediction of aromatic character polycyclic hydrocarbons. Using a small set building blocks combination rules, demonstrate simple intuitive construction complete NICS-XY-scans several test cases one- two-dimensional systems comprising six-membered rings. Partitioning contribution discrete provides...
The 17 isomers of the [4]- and [5]phenylenes have been studied with three different computational levels current-density analysis (CDA) by calculation out-of-plane contribution to nucleus-independent chemical shifts (NICS(πzz)). Current-density maps for these isomeric phenylenes are typically dominated strong paratropic ring currents in four-membered rings. relative energies isomers, which differ only through effects differential strain aromaticity, were computed at B3LYP/6-311G* level. It...