A5090312504- X-ray Diffraction in Crystallography
- Crystallization and Solubility Studies
- Luminescence and Fluorescent Materials
- Cyclopropane Reaction Mechanisms
- Chemical Synthesis and Analysis
- Synthesis and Reactivity of Heterocycles
- Phosphorus compounds and reactions
- Synthesis and Biological Evaluation
- Mechanical and Optical Resonators
- Organic Electronics and Photovoltaics
- Force Microscopy Techniques and Applications
- Synthesis and Catalytic Reactions
- Conducting polymers and applications
- Carbon Nanotubes in Composites
- Photoacoustic and Ultrasonic Imaging
- Supramolecular Chemistry and Complexes
- Sulfur-Based Synthesis Techniques
- Synthesis of heterocyclic compounds
- Photochromic and Fluorescence Chemistry
- Nonlinear Optical Materials Research
- Synthesis and Properties of Aromatic Compounds
- Synthesis and biological activity
California Institute of Technology
2022-2023
Macalester College
2019-2022
External control of chemical reactions in biological settings with spatial and temporal precision is a grand challenge for noninvasive diagnostic therapeutic applications. While light conventional stimulus remote activation, its penetration severely attenuated tissues, which limits applicability. On the other hand, ultrasound biocompatible energy source that highly penetrant offers wide range functional tunability. Coupling to activation specific under physiological conditions, however,...
This work describes a three-step chromatography-free protocol for the synthesis of novel organic materials building block, dichlorinated mellophanic diimide (MDI), that is shown to undergo nucleophilic substitution with variety ortho disubstituted benzenes yield series chromophores. Furthermore, 1,2,4,5-tetrasubstituted can be used synthesize tetraimide heteropentacene derivatives endcapped by MDI motifs. The fine-tuning effects heteroatom identity were investigated UV–vis and fluorescence...
During the past two decades, our understanding of mechanochemical reactivity has advanced considerably. Nevertheless, an incomplete knowledge structure-activity relationships and principles that govern transformations limits molecular design. The experimental development mechanophores thus benefited from simple computational tools like CoGEF, which quantitative metrics rupture force can be extracted to estimate reactivity. Furan-maleimide (FM) anthracene-maleimide (AM) Diels-Alder adducts...
Abstract Ultra‐electron‐deficient azaacenes were synthesized via Buchwald‐Hartwig coupling of ortho‐ diaminoarenes with chlorinated mellophanic diimide followed by oxidation the intermediate N , N’ ‐dihydro compounds MnO 2 or PbO . The resulting cata ‐annulated bisimide have ultrahigh electron affinities first reduction potentials as low −0.35 V recorded for a tetraazapentacene. Attempts to prepare tetrakis(dicarboximide)tetraazaheptacene resulted in formation symmetric butterfly dimer.
The preparation of halogenated benzene-1,2,3,4-tetracarboxylic diimide derivatives is challenging because the possibility competitive incorrect cyclizations and SNAr reactivity. Here, we demonstrate that bypassing traditional cyclic anhydrides instead directly reacting dihalobenzene-1,2,3,4-tetracarboxylic acids with primary amines in acetic acid solvent successfully provides a range desirable ortho-diimide products good yields. Furthermore, sterically N-derivatizations can be readily...
This work describes the unexpected formation of an unusual phosphonium ylide when attempting synthesis bisphosphonium pyromellitic diimides. Spectroscopic and crystallographic characterization reveals that a combination π-π CH⋅⋅⋅O interactions leads to supramolecular homodimerization both in solution solid-state. Only strong acids are able protonate ylide, which is otherwise inert Wittig alkylation reactivity. Taken together, these observations indicate this compound one most highly...
This work describes a three-step chromatography-free protocol for the synthesis of novel organic materialsbuilding block, dichlorinated mellophanic diimide (MDI), that is shown to undergo nucleophilic substitutionwith variety ortho disubstituted benzenes yield series chromophores. Furthermore, 1,2,4,5-tetrasubstituted can be used synthesize tetraimide heteropentacene derivatives endcapped byMDI motifs. The fine-tuning effects heteroatom identity were investigated by UV-Vis and...
The preparation of halogenated benzene-1,2,3,4-tetracarboxylic diimide derivatives is challenging because the possibility competitive incorrect cyclizations and SNAr reactivity. Here, we demonstrate that direct reaction acids with primary amines in acetic acid solvent successfully provides a range desirable ortho-diimide products good yields. Furthermore, sterically N-derivatizations can be readily achieved under microwave reactor conditions, reactivity only observed when excess amine used....
<div>This work describes a three-step chromatography-free protocol for the synthesis of novel organic materials</div><div>building block, dichlorinated mellophanic diimide (MDI), that is shown to undergo nucleophilic substitution</div><div>with variety ortho disubstituted benzenes yield series chromophores. Furthermore, 1,2,4,5-</div><div>tetrasubstituted can be used synthesize tetraimide heteropentacene derivatives endcapped...
This work describes the unexpected formation of an unusual phosphonium ylide when attempting synthesis bisphosphonium pyromellitic diimides. Spectroscopic and crystallographic characterization reveals that a combination π-π CH•••O interactions leads to supramolecular homodimerization both in solution solid-state. Only strong acids are able protonate ylide, which is otherwise inert Wittig alkylation reactivity. Taken together, these observations indicate this compound one most highly...
This work describes the unexpected formation of an unusual phosphonium ylide when attempting synthesis bisphosphonium pyromellitic diimides. Spectroscopic and crystallographic characterization reveals that a combination π-π CH•••O interactions leads to supramolecular homodimerization both in solution solid-state. Only strong acids are able protonate ylide, which is otherwise inert Wittig alkylation reactivity. Taken together, these observations indicate this compound one most highly...
The preparation of halogenated benzene-1,2,3,4-tetracarboxylic diimide derivatives is challenging because the possibility competitive incorrect cyclizations and SNAr reactivity. Here, we demonstrate that direct reaction acids with primary amines in acetic acid solvent successfully provides a range desirable ortho-diimide products good yields. Furthermore, sterically N-derivatizations can be readily achieved under microwave reactor conditions, reactivity only observed when excess amine used....