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Papers by Jack Ly

Metallaphotoredox catalysis combines the well-established mechanisms of transition-metal-catalyze... more Metallaphotoredox catalysis combines the well-established mechanisms of transition-metal-catalyzed cross-coupling reactions with one-electron redox manipulations enabled by light. In most cases, a transition metal or organic dye serves as the photoredox catalyst while a ground-state Pd or Ni catalyst performs the organometallic steps. Cross-coupling mechanisms that rely on direct photoexcitation of a light-absorbing substrate have the potential to access distinct mechanisms and deliver unique selectivity based on the substrate’s excited-state properties. In this report, we describe a photoinduced, Ni-catalyzed Suzuki–Miyaura cross coupling reaction that selectively functionalizes BODIPY chromophores, a versatile class of tunable, bright, photostable fluorophores. Using a bis-iodo BODIPY substrate, the selectivity for mono- vs. bis-arylation was found to be governed by a remote substituent that subtly alters the excited-state properties of the substrate. Consistent with a substrate p...

Physical Chemistry Chemical Physics

Ten methylated-meso-phenyl-BODIPY dyes with varying iodine content were synthesized and studied u... more Ten methylated-meso-phenyl-BODIPY dyes with varying iodine content were synthesized and studied using experimental and theoretical methods to examine how iodine substitution and loading influence the excited-state dynamics of the chromophores.

Sensors and Actuators B: Chemical

MEDICAL DEVICES & SENSORS

This is the author manuscript accepted for publication and has undergone full peer review but has... more This is the author manuscript accepted for publication and has undergone full peer review but has not been through the copyediting, typesetting, pagination and proofreading process, which may lead to differences between this version and the Version of Record. Please cite this article as

The Journal of Physical Chemistry A

The authors would like to add missing references to the crystallography data of Rub-2 and Rub-3. ... more The authors would like to add missing references to the crystallography data of Rub-2 and Rub-3. In the Molecular and Crystal Geometries section of the initial report, the crystal structures of Rub-2 (CSD-POGZIV) and Rub-3 (CSD-PIXPOD01) were obtained from the Cambridge Crystallographic Data Centre (CCDC) produced from previous work by Hou et al. and Mamada et al., respectively. 1−3 These corrections do not affect the conclusions of this work, and the authors regret the oversight. All authors have approved this correction.

The Journal of Physical Chemistry A

Journal of Materials Chemistry C

In studying the formation and thermally activated cycloreversion of oxidized rubrene to pristine ... more In studying the formation and thermally activated cycloreversion of oxidized rubrene to pristine rubrene, we observed an irreversible, second stage oxidized product. Understanding the formation of the irreversible adduct will help one design more chemically robust rubrene derivatives.

Advanced Materials Interfaces

ACS Applied Materials & Interfaces

An all-acceptor napthalenediimide-bithiazole based copolymer, P(NDI2OD-BiTz), was synthesized and... more An all-acceptor napthalenediimide-bithiazole based copolymer, P(NDI2OD-BiTz), was synthesized and characterized for application in thin film transistors. DFT calculations point to an optimal perpendicular dihedral angle of 90° between acceptor units along isolated polymer chains; yet optimized transistors yield electron mobilities of 0.11 cm2/Vs with the use of a zwitterionic naphthalenediimide interlayer. GIXD measurements of annealed films reveal P(NDI2OD-BiTz) adopts a highly ordered edge-on orientation, exact opposite to similar bithiophene analogues. This report highlights an NDI and thiazole all-acceptor polymer and demonstrates high electron mobility despite its non-planar backbone conformation.

Chemistry of Materials, 2016

Abstracts of Papers of the American Chemical Society, 2011

Abstracts of Papers of the American Chemical Society, 2011

The self-assembly of amphiphilic block copolymers is dictated primarily by the balance between th... more The self-assembly of amphiphilic block copolymers is dictated primarily by the balance between the hydrophobic core volume and the hydrophilic corona. In these studies, ABA and BAB triblock copolymers containing poly(lysine) (PK) and poly(propylene oxide) were synthesized and their solution properties studied using dynamic light scattering, circular dichroism spectroscopy and transmission electron microscopy. This talk will present some recent studies in solution morphology transitions that occur in these materials as a result of the helix-coil transition and associated charge-charge interactions. The solution properties and responsiveness of these novel materials will be discussed in terms of their ability to encapsulate and deliver cancer therapeutics.

Polymer Chemistry, 2011

The following data are provided in support of this manuscript: Figure S1 presents quantitative 13... more The following data are provided in support of this manuscript: Figure S1 presents quantitative 13 C NMR for the thiol-yne conjugation to form Chol 2 PBLG 11 and POSS 2 PBLG 11 , Figure S2 presents angle-dependent DLS decay rate data to verify Brownian diffusion of spherical particles and to calculate D app , Figure S3 shows DMF GPC traces for two samples, Figure S4 shows the kinetics associated with a pH jump in terms of scattered intensity and Figure S5 shows how 13 C NMR. Bis-addition resonances show up at ~ 44 and 35 ppm for thiol carbon from Chol, 45 and 37 ppm for thiol carbon from POSS. Unfortunately, peaks associated with cholesterol show up in this region as well. For POSS-addition, 2 carbons from POSS show up around 35 ppm. For mono-addition at C(1), the alkene carbons would appear at 134 and 117, which is interfered with by aromatic carbons from benzyl protecting group of the polypeptide. For mono-addition at C(2), peaks would be present at 153 (next to thio ether) and 97 ppm. For no additions (unreacted peptide) peaks would be present at ~ 68 and 80 ppm. Furthermore, when referring back to 1 H NMR, two additions would show up at ~ 2.8 and 3.4 ppm as well as the methylene next to amide on the end group shifting from 3.9 to 3.5. If mono-addition was present, there would be no shift in the methylene (we see it disappear) and protons associated with the alkene would be present at ~ 6.3 and 5.4 ppm (we do not observe that). For mono-addition at C(2), methylene

Macromolecular Rapid Communications, 2012

We report the synthesis and solution characterization of poly(L-lysine)-b-poly(propylene oxide)-b... more We report the synthesis and solution characterization of poly(L-lysine)-b-poly(propylene oxide)-b-poly(L-lysine) (KPK) triblock copolymers with high lysine weight fractions (>75 wt%). In contrast to PK diblock copolymers in this composition range, KPK triblock copolymers exhibit morphology transitions as a function of pH. Using a combination of light-scattering and microscopy techniques, we demonstrate spherical micelle-vesicle and spherical micelle-disk micelle transitions for different K fractions. We interpret these morphology changes in terms of the energy penalty associated with folding the core P block to form a spherical micelle in relation to the interfacial curvature associated with different charged states of the K block.

Bulletin of the American Physical …, 2011

Stimuli-responsive copolymers demonstrate diverse aggregation behavior in aqueous solution. In ge... more Stimuli-responsive copolymers demonstrate diverse aggregation behavior in aqueous solution. In general, the molecular architecture and the balance of hydrophilic and hydrophobic volumes influence morphology. This study involves polypeptide-based ABA linear triblock ...

Macromolecular Rapid Communications, 2012

Metallaphotoredox catalysis combines the well-established mechanisms of transition-metal-catalyze... more Metallaphotoredox catalysis combines the well-established mechanisms of transition-metal-catalyzed cross-coupling reactions with one-electron redox manipulations enabled by light. In most cases, a transition metal or organic dye serves as the photoredox catalyst while a ground-state Pd or Ni catalyst performs the organometallic steps. Cross-coupling mechanisms that rely on direct photoexcitation of a light-absorbing substrate have the potential to access distinct mechanisms and deliver unique selectivity based on the substrate’s excited-state properties. In this report, we describe a photoinduced, Ni-catalyzed Suzuki–Miyaura cross coupling reaction that selectively functionalizes BODIPY chromophores, a versatile class of tunable, bright, photostable fluorophores. Using a bis-iodo BODIPY substrate, the selectivity for mono- vs. bis-arylation was found to be governed by a remote substituent that subtly alters the excited-state properties of the substrate. Consistent with a substrate p...

Physical Chemistry Chemical Physics

Ten methylated-meso-phenyl-BODIPY dyes with varying iodine content were synthesized and studied u... more Ten methylated-meso-phenyl-BODIPY dyes with varying iodine content were synthesized and studied using experimental and theoretical methods to examine how iodine substitution and loading influence the excited-state dynamics of the chromophores.

Sensors and Actuators B: Chemical

MEDICAL DEVICES & SENSORS

This is the author manuscript accepted for publication and has undergone full peer review but has... more This is the author manuscript accepted for publication and has undergone full peer review but has not been through the copyediting, typesetting, pagination and proofreading process, which may lead to differences between this version and the Version of Record. Please cite this article as

The Journal of Physical Chemistry A

The authors would like to add missing references to the crystallography data of Rub-2 and Rub-3. ... more The authors would like to add missing references to the crystallography data of Rub-2 and Rub-3. In the Molecular and Crystal Geometries section of the initial report, the crystal structures of Rub-2 (CSD-POGZIV) and Rub-3 (CSD-PIXPOD01) were obtained from the Cambridge Crystallographic Data Centre (CCDC) produced from previous work by Hou et al. and Mamada et al., respectively. 1−3 These corrections do not affect the conclusions of this work, and the authors regret the oversight. All authors have approved this correction.

The Journal of Physical Chemistry A

Journal of Materials Chemistry C

In studying the formation and thermally activated cycloreversion of oxidized rubrene to pristine ... more In studying the formation and thermally activated cycloreversion of oxidized rubrene to pristine rubrene, we observed an irreversible, second stage oxidized product. Understanding the formation of the irreversible adduct will help one design more chemically robust rubrene derivatives.

Advanced Materials Interfaces

ACS Applied Materials & Interfaces

An all-acceptor napthalenediimide-bithiazole based copolymer, P(NDI2OD-BiTz), was synthesized and... more An all-acceptor napthalenediimide-bithiazole based copolymer, P(NDI2OD-BiTz), was synthesized and characterized for application in thin film transistors. DFT calculations point to an optimal perpendicular dihedral angle of 90° between acceptor units along isolated polymer chains; yet optimized transistors yield electron mobilities of 0.11 cm2/Vs with the use of a zwitterionic naphthalenediimide interlayer. GIXD measurements of annealed films reveal P(NDI2OD-BiTz) adopts a highly ordered edge-on orientation, exact opposite to similar bithiophene analogues. This report highlights an NDI and thiazole all-acceptor polymer and demonstrates high electron mobility despite its non-planar backbone conformation.

Chemistry of Materials, 2016

Abstracts of Papers of the American Chemical Society, 2011

Abstracts of Papers of the American Chemical Society, 2011

The self-assembly of amphiphilic block copolymers is dictated primarily by the balance between th... more The self-assembly of amphiphilic block copolymers is dictated primarily by the balance between the hydrophobic core volume and the hydrophilic corona. In these studies, ABA and BAB triblock copolymers containing poly(lysine) (PK) and poly(propylene oxide) were synthesized and their solution properties studied using dynamic light scattering, circular dichroism spectroscopy and transmission electron microscopy. This talk will present some recent studies in solution morphology transitions that occur in these materials as a result of the helix-coil transition and associated charge-charge interactions. The solution properties and responsiveness of these novel materials will be discussed in terms of their ability to encapsulate and deliver cancer therapeutics.

Polymer Chemistry, 2011

The following data are provided in support of this manuscript: Figure S1 presents quantitative 13... more The following data are provided in support of this manuscript: Figure S1 presents quantitative 13 C NMR for the thiol-yne conjugation to form Chol 2 PBLG 11 and POSS 2 PBLG 11 , Figure S2 presents angle-dependent DLS decay rate data to verify Brownian diffusion of spherical particles and to calculate D app , Figure S3 shows DMF GPC traces for two samples, Figure S4 shows the kinetics associated with a pH jump in terms of scattered intensity and Figure S5 shows how 13 C NMR. Bis-addition resonances show up at ~ 44 and 35 ppm for thiol carbon from Chol, 45 and 37 ppm for thiol carbon from POSS. Unfortunately, peaks associated with cholesterol show up in this region as well. For POSS-addition, 2 carbons from POSS show up around 35 ppm. For mono-addition at C(1), the alkene carbons would appear at 134 and 117, which is interfered with by aromatic carbons from benzyl protecting group of the polypeptide. For mono-addition at C(2), peaks would be present at 153 (next to thio ether) and 97 ppm. For no additions (unreacted peptide) peaks would be present at ~ 68 and 80 ppm. Furthermore, when referring back to 1 H NMR, two additions would show up at ~ 2.8 and 3.4 ppm as well as the methylene next to amide on the end group shifting from 3.9 to 3.5. If mono-addition was present, there would be no shift in the methylene (we see it disappear) and protons associated with the alkene would be present at ~ 6.3 and 5.4 ppm (we do not observe that). For mono-addition at C(2), methylene

Macromolecular Rapid Communications, 2012

We report the synthesis and solution characterization of poly(L-lysine)-b-poly(propylene oxide)-b... more We report the synthesis and solution characterization of poly(L-lysine)-b-poly(propylene oxide)-b-poly(L-lysine) (KPK) triblock copolymers with high lysine weight fractions (>75 wt%). In contrast to PK diblock copolymers in this composition range, KPK triblock copolymers exhibit morphology transitions as a function of pH. Using a combination of light-scattering and microscopy techniques, we demonstrate spherical micelle-vesicle and spherical micelle-disk micelle transitions for different K fractions. We interpret these morphology changes in terms of the energy penalty associated with folding the core P block to form a spherical micelle in relation to the interfacial curvature associated with different charged states of the K block.

Bulletin of the American Physical …, 2011

Stimuli-responsive copolymers demonstrate diverse aggregation behavior in aqueous solution. In ge... more Stimuli-responsive copolymers demonstrate diverse aggregation behavior in aqueous solution. In general, the molecular architecture and the balance of hydrophilic and hydrophobic volumes influence morphology. This study involves polypeptide-based ABA linear triblock ...

Macromolecular Rapid Communications, 2012