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  1. Article ; Online: Pnictogen-Rich Heterocycles Derived from a Phosphadiazonium Cation.

    Milkovich, Shaun K / Buguis, Francis L / Boyle, Paul D / Gilroy, Joe B

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2024  Volume 30, Issue 25, Page(s) e202400569

    Abstract: Heterocycles that pair main group elements and nitrogen are extremely important within the π-conjugated heterocycles research community. Compared to the vast number of boron-nitrogen heterocycles, those that include phosphorus are less common. ... ...

    Abstract Heterocycles that pair main group elements and nitrogen are extremely important within the π-conjugated heterocycles research community. Compared to the vast number of boron-nitrogen heterocycles, those that include phosphorus are less common. Furthermore, the use of phosphorus-nitrogen triple bonds of any type to prepare such compounds is unprecedented. Here, we pair pyridyl hydrazonide ligands with phosphadiazonium cations and demonstrate that the chelated Mes*NP group is directly implicated in the photophysical and redox properties observed for the resulting heterocycles. In doing so, we introduce a novel building block for the production of phosphorus-containing heterocycles that could find use in small molecule activation and catalysis or as the functional component of emerging organic electronics.
    Language English
    Publishing date 2024-03-13
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202400569
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  2. Article ; Online: Tuning the Properties of Donor-Acceptor and Acceptor-Donor-Acceptor Boron Difluoride Hydrazones

    Cappello, Daniela / Buguis, Francis L / Gilroy, Joe B

    ACS omega

    2022  Volume 7, Issue 36, Page(s) 32727–32739

    Abstract: Molecular materials with π-conjugated donor-acceptor (D-A) and acceptor-donor-acceptor (A-D-A) electronic structures have received significant attention due to their usage in organic photovoltaic materials, in organic light-emitting diodes, and as ... ...

    Abstract Molecular materials with π-conjugated donor-acceptor (D-A) and acceptor-donor-acceptor (A-D-A) electronic structures have received significant attention due to their usage in organic photovoltaic materials, in organic light-emitting diodes, and as biological imaging agents. Boron-containing molecular materials have been explored as electron-accepting units in compounds with D-A and A-D-A properties as they often exhibit unique and tunable optoelectronic and redox properties. Here, we utilize Stille cross-coupling chemistry to prepare a series of compounds with boron difluoride hydrazones (BODIHYs) as acceptors and benzene, thiophene, or 9,9-dihexylfluorene as donors. BODIHYs with D-A and A-D-A properties exhibited multiple reversible redox waves, solid-state emission with photoluminescence quantum yields up to 10%, and aggregation-induced emission (AIE). Optical band gaps (or highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gaps) determined for these compounds (2.02-2.25 eV) agree well with those determined from cyclic voltammetry experiments (2.05-2.42 eV). The optoelectronic properties described herein are rationalized with density functional theory calculations that support the interpretation of the experimental findings. This work provides a foundation of understanding that will allow for the consideration of D-A and A-D-A BODIHYs to be incorporated into applications (
    Language English
    Publishing date 2022-08-26
    Publishing country United States
    Document type Journal Article
    ISSN 2470-1343
    ISSN (online) 2470-1343
    DOI 10.1021/acsomega.2c04401
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  3. Article ; Online: Formazanate coordination compounds: synthesis, reactivity, and applications.

    Gilroy, Joe B / Otten, Edwin

    Chemical Society reviews

    2019  Volume 49, Issue 1, Page(s) 85–113

    Abstract: Formazans (Ar1-NH-N[double bond, length as m-dash]CR3-N[double bond, length as m-dash]N-Ar5), a class of nitrogen-rich and highly colored compounds, have been known since the late 1800s and studied more closely since the early 1940s. Their intense color ... ...

    Abstract Formazans (Ar1-NH-N[double bond, length as m-dash]CR3-N[double bond, length as m-dash]N-Ar5), a class of nitrogen-rich and highly colored compounds, have been known since the late 1800s and studied more closely since the early 1940s. Their intense color has led to their widespread use as dyes, especially in cell biology where they are most often used to quantitatively assess cell-viability. Despite structural similarities to well-known ligand classes such as β-diketiminates, the deprotonated form of formazans, formazanates, have received relatively little attention in the transition metal and main group coordination chemistry arenas. Formazanate ligands benefit from tunable properties via structural variation, rich optoelectronic properties owing to their highly delocalized π-systems, low-lying frontier orbitals that stabilize otherwise highly reactive species such as radicals, and redox activity and coordinative flexibility that may have significant implications in their future use in catalysis. Here, we review progress in the coordination chemistry of formazanate ligands over the past two decades, with emphasis on the reactivity and applications of the subsequent complexes.
    Language English
    Publishing date 2019-12-03
    Publishing country England
    Document type Journal Article ; Review
    ZDB-ID 1472875-8
    ISSN 1460-4744 ; 0306-0012
    ISSN (online) 1460-4744
    ISSN 0306-0012
    DOI 10.1039/c9cs00676a
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  4. Article ; Online: Group 13 Complexes of Chelating N

    Maar, Ryan R / Gilroy, Joe B

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2018  Volume 24, Issue 48, Page(s) 12449–12457

    Abstract: Recent synthetic advances have afforded opportunities for the creation of a wide range of potentially tetradentate ... ...

    Abstract Recent synthetic advances have afforded opportunities for the creation of a wide range of potentially tetradentate N
    Language English
    Publishing date 2018-06-12
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-x
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.201800354
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  5. Article ; Online: A Boron Difluoride Hydrazone (BODIHY) Polymer Exhibits Aggregation-Induced Emission.

    Cappello, Daniela / Watson, Alexander E R / Gilroy, Joe B

    Macromolecular rapid communications

    2020  Volume 42, Issue 8, Page(s) e2000553

    Abstract: Polymers that exhibit aggregation-induced emission (AIE) find use, for example, as cell-imaging agents and as fluorometric sensors due to their unique optical properties. However, the structural diversity of AIE-active polymers has not necessarily ... ...

    Abstract Polymers that exhibit aggregation-induced emission (AIE) find use, for example, as cell-imaging agents and as fluorometric sensors due to their unique optical properties. However, the structural diversity of AIE-active polymers has not necessarily advanced at the same rate as their applications. In this work, ring-opening metathesis polymerization is used to synthesize the first example of a polymer (M
    MeSH term(s) Boron Compounds ; Hydrazones ; Polymerization ; Polymers
    Chemical Substances Boron Compounds ; Hydrazones ; Polymers ; boron difluoride
    Language English
    Publishing date 2020-12-04
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1475027-2
    ISSN 1521-3927 ; 1022-1336
    ISSN (online) 1521-3927
    ISSN 1022-1336
    DOI 10.1002/marc.202000553
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  6. Article ; Online: Band Gap Engineering in Acceptor-Donor-Acceptor Boron Difluoride Formazanates.

    Dhindsa, Jasveer S / Buguis, Francis L / Anghel, Michael / Gilroy, Joe B

    The Journal of organic chemistry

    2021  Volume 86, Issue 17, Page(s) 12064–12074

    Abstract: π-Conjugated molecules with acceptor-donor-acceptor (A-D-A) electronic structures make up an important class of materials due to their tunable optoelectronic properties and applications in, for example, organic light-emitting diodes, nonlinear optical ... ...

    Abstract π-Conjugated molecules with acceptor-donor-acceptor (A-D-A) electronic structures make up an important class of materials due to their tunable optoelectronic properties and applications in, for example, organic light-emitting diodes, nonlinear optical devices, and organic solar cells. The frontier molecular orbital energies, and thus band gaps, of these materials can be tuned by varying the donor and acceptor traits and π-electron counts of the structural components. Herein, we report the synthesis and characterization of a series of A-D-A compounds consisting of BF
    Language English
    Publishing date 2021-08-06
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c01416
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  7. Article ; Online: Near-Infrared Boron Difluoride Formazanate Dyes.

    Buguis, Francis L / Maar, Ryan R / Staroverov, Viktor N / Gilroy, Joe B

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 27, Issue 8, Page(s) 2854–2860

    Abstract: Near-infrared (NIR) dyes are sought after for their utility in light harvesting, bioimaging, and light-mediated therapies. Since long-wavelength photoluminescence typically involves extensive π-conjugated systems of double bonds and aromatic rings, it is ...

    Abstract Near-infrared (NIR) dyes are sought after for their utility in light harvesting, bioimaging, and light-mediated therapies. Since long-wavelength photoluminescence typically involves extensive π-conjugated systems of double bonds and aromatic rings, it is often assumed that NIR dyes have to be large molecules that require complex syntheses. We challenge this assumption by demonstrating that facile incorporation of tertiary amine groups into readily available 3-cyanoformazans affords efficient production of relatively simple NIR-active BF
    Language English
    Publishing date 2021-01-14
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202004793
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  8. Article ; Online: Heterocyclic Phosphenium Cations and Their Divergent Coordination Chemistry.

    Watson, Alexander E R / Grant, Michael J / Boyle, Paul D / Ragogna, Paul J / Gilroy, Joe B

    Inorganic chemistry

    2022  Volume 61, Issue 46, Page(s) 18719–18728

    Abstract: While they are often encountered as reaction intermediates, phosphenium cations are not commonly incorporated into π-conjugated systems. We report the synthesis and characterization of donor-stabilized phosphenium cations supported by pyridylhydrazonide ... ...

    Abstract While they are often encountered as reaction intermediates, phosphenium cations are not commonly incorporated into π-conjugated systems. We report the synthesis and characterization of donor-stabilized phosphenium cations supported by pyridylhydrazonide ligands. The preparation of these cations relies on precise control of ligand
    Language English
    Publishing date 2022-11-10
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1484438-2
    ISSN 1520-510X ; 0020-1669
    ISSN (online) 1520-510X
    ISSN 0020-1669
    DOI 10.1021/acs.inorgchem.2c03216
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  9. Article ; Online: Multicomponent Synthesis of Poly(α-aminophosphine chalcogenide)s and Subsequent Depolymerization.

    Lamberink-Ilupeju, Jan-Willem / Willans, Mathew J / Gilroy, Joe B / Noël, James J / Blacquiere, Johanna M / Ragogna, Paul J

    Inorganic chemistry

    2023  Volume 62, Issue 37, Page(s) 15104–15109

    Abstract: Multicomponent reactions of primary phosphines (R- ... ...

    Abstract Multicomponent reactions of primary phosphines (R-PH
    Language English
    Publishing date 2023-09-07
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1484438-2
    ISSN 1520-510X ; 0020-1669
    ISSN (online) 1520-510X
    ISSN 0020-1669
    DOI 10.1021/acs.inorgchem.3c02039
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  10. Article ; Online: Dyads and Triads of Boron Difluoride Formazanate and Boron Difluoride Dipyrromethene Dyes.

    Buguis, Francis L / Hsu, Nathan Sung Y / Sirohey, Sofia A / Adam, Matheus C / Goncharova, Lyudmila V / Gilroy, Joe B

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2023  Volume 29, Issue 71, Page(s) e202302548

    Abstract: Dye-dye conjugates have attracted significant interest for their utility in applications such as bioimaging, theranostics, and light-harvesting. Many classes of organic dyes have been employed in this regard; however, building blocks don't typically ... ...

    Abstract Dye-dye conjugates have attracted significant interest for their utility in applications such as bioimaging, theranostics, and light-harvesting. Many classes of organic dyes have been employed in this regard; however, building blocks don't typically extend beyond small chromophores. This can lead to minor changes to the optoelectronic properties of the original dye. The exploration of dye-dye structures is impeded by long synthetic routes, incompatible synthetic conditions, or a mismatch of the desired properties. Here, we present the first-of-their-kind dye-dye conjugates of boron difluoride complexes of formazanate and dipyrromethene ligands. These conjugates exhibit dual photoluminescence bands that reach the near-infrared spectral region and implicate anti-Kasha processes. Cyclic voltammetry experiments revealed the generation of polyanionic species that can reversibly tolerate the uptake of up to 6 electrons. Ultimately, we demonstrate that BF
    Language English
    Publishing date 2023-11-02
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202302548
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