A5079258753- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Synthesis and Properties of Aromatic Compounds
- Organic Electronics and Photovoltaics
- Luminescence and Fluorescent Materials
- Molecular Junctions and Nanostructures
- Fullerene Chemistry and Applications
- Radical Photochemical Reactions
- Catalytic C–H Functionalization Methods
- Organic and Molecular Conductors Research
- Oxidative Organic Chemistry Reactions
- Crystallography and molecular interactions
- Advanced battery technologies research
- Synthesis and properties of polymers
- Biodiesel Production and Applications
- Catalysis and Hydrodesulfurization Studies
- Magnetism in coordination complexes
- Cyclization and Aryne Chemistry
- Advanced Chemical Physics Studies
- Catalytic Alkyne Reactions
- Organic Light-Emitting Diodes Research
- Supramolecular Chemistry and Complexes
- Catalysis for Biomass Conversion
University of Oregon
2014-2019
Eugene Research Institute
2016-2019
Hendrix College
2013
Conway School of Landscape Design
2013
Ames National Laboratory
2013
Highly conjugated hydrocarbons have attracted interest for use as active materials in electronic devices such organic field effect transistors (OFET) and photovoltaics (OPV). In this Account, we review our progress synthesizing studying a new class of small molecules potential semiconductors. The idea originated from prior research on octadehydrodibenz[12]annulene, the system can undergo double transannular cyclization to yield indeno[1,2-b]fluorene skeleton. Subsequent functionalization...
Understanding and controlling the electronic structure of molecules is crucial when designing optimizing new organic semiconductor materials. We report regioselective synthesis eight π-expanded diarenoindacene analogues based on indeno[1,2-b]fluorene framework along with computational investigation an array diareno-fused antiaromatic compounds possessing s-indacene, pentalene, or cyclobutadiene cores. Analysis experimental computationally derived optoelectronic properties uncovered a linear...
Exchanging fused benzenes for benzothiophenes results in pronounced antiaromaticity the indacene core.
The synthesis and optoelectronic properties of 24 π-electron, formally antiaromatic fluoreno[3,2-b]fluorene fluoreno[4,3-c]fluorene (FF), are presented. solid-state structure [4,3-c]FF along with computationally analogous molecules shows that the outer rings aromatic while central four possess a bond-localized 2,6-naphthoquinodimethane motif. antiaromaticity biradical character FFs is assessed computationally, results which indicate dominance closed-shell ground state for these molecules.
Charge-carrier transport in thin-film organic semiconductors is strongly related to the molecular structure and solid-state packing, which turn are dependent on materials processing device configurations. We report synthesis characterization of a series (trialkylsilyl)ethynyl-substituted dinaphtho-fused s-indacenes that include three regioisomers: linear, syn, anti isomers. Structure–property relationships established for these antiaromatic compounds by combining X-ray diffraction with...
A hybrid adsorbent-catalytic nanostructured material consisting of aminopropyl groups and nickel nanoparticles immobilized in mesoporous silica (AP-Ni-MSN) was employed to selectively capture free fatty acids (FFAs) convert them into saturated hydrocarbons. The working principle these sorbent-catalytic particles initially tested the hydrogenation oleic acid. Besides providing selectivity for FFAs, adsorbent also affected reaction, shifting chemistry from hydrocracking-based (Ni)...
We report the synthesis of donor-acceptor-donor triads based on indeno[1,2-b]fluorene-6,12-dione (IF) scaffold. Arylethynyl donor group attachment expands light absorption these molecules to 600-700 nm region compared derivatives with nondonating silylethynyl substituents yet does not affect electron-accepting capabilities IF core. All show reduction potentials at similar or less negative derivatives. Protonation studies using bis(dibutylanilino) triad verify charge transfer nature expanded profile.
A set of fully-conjugated indenofluorenes has been synthesized and confirmed by solid-state structure analysis. The indeno[2,1-c]fluorenes their benzo-fused analogues all contain the antiaromatic as-indacene core. molecules possess high electron affinities show a broad absorption that reaches into near-IR region electromagnetic spectrum. All featured compounds reversibly accept up to two electrons as revealed cyclic voltammetry. Analysis molecule tropicity using NICS-XY scan calculations...
An <italic>ortho</italic>-naphtho diradical! Quinoidal forms in <italic>para</italic>- and <italic>meta</italic>-patterns lie at the extremes for closed-shell diradical fluorenofluorenes, respectively. <italic>ortho</italic>-Conjugation gives an intermediate case with partial character.
Abstract Redox‐controlled dimerization of tetrathiafulvalene (TTF) derivatives is an important tool for achieving reversible assemblies. Herein, the synthesis and characterization indacene–TTF hybrids, in which central core fused to naphtho or benzothieno units, are reported. The orientation these units has a strong influence on redox properties, with regard number electrons involved first oxidation event ability oxidized forms associate. formation mixed‐valence π‐dimer complexes turned off...
A freely soluble dianthracenoindacene derivative has been synthesized using an ‘inside-out’ Friedel–Crafts alkylation method and is the first fluorescent diacenoindacene reported. Linear fusion of anthracenes confirmed by X-ray diffraction studies on neutral molecule as well its dianion. Based predictions from our previous studies, this also least antiaromatic yet to be prepared, which reflected in highly negative irreversible reduction. With paratropicity essentially eliminated, we posit...
The serendipitous isolation of very small amounts two naphthocyclobutadiene (NCB) derivatives has led to the computational re-examination electrocyclization Z,Z-3,5-octadiene-1,7-diyne as well experimental and study diethynylindeno[2,1-a]fluorene that contain 3,5-octadiene-1,7-diyne motif part a larger π-framework. In both cases calculated potential energy surface strongly implicates successive electrocyclic reactions afford antiaromatic products. With octadienediyne fragment locked in...
Abstract The process proceeds through formation of iminium ions which are trapped by the internal OH group.