All posts by administrador

2020, AzaBN, Publicación

Abengozar et al. Chem Commun (Camb). 2020;56(25):3669-3672. Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene.

Publications > Abengozar et al

Chem Commun 2020, 56, 3669 PubMed 32115593

Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene.

Alberto Abengozara, Isabel Valencia, Guillermo G Otarola, David Sucunza, Patricia Garcia-Garcia, Adrian Perez-Redondo, Francisco Mendicuti, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR), Universidad de Alcala, IRYCIS, 28805 Alcala de Henares, Spain.

a. david.sucunza@uah.es, juanjose.vaquero@uah.es

Abstract

Previously unknown 4a-aza-12a-borachrysene has been synthesized in only four steps. The reactions of this BN-embedded PAH with bromine and organolithium compounds proceed with complete regioselectivity, resulting in the formation of nine derivatives. One of these, a phenylalkynyl-substituted derivative, exhibits a remarkably high fluorescence quantum yield (PhiF = 0.68).

Noticias

ChemComm 03.2020

Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene

Alberto Abengózar,‡ Isabel Valencia,‡ Guillermo G. Otárola, David Sucunza,* Patricia García-García, Adrián Pérez-Redondo, Francisco Mendicuti and Juan J. Vaquero*

Chem. Commun., 2020, Advance Article
DOI: 10.1039/C9CC09998K

Previously unknown 4a-aza-12a-borachrysene has been synthesized in only four steps. The reactions of this BN-embedded PAH with bromine and organolithium compounds proceed with complete regioselectivity, resulting in the formation of nine derivatives. One of these, a phenylalkynyl-substituted derivative, exhibits a remarkably high fluorescence quantum yield (ΦF = 0.68).

2020, BioImag, Publicación

Garre et al. J Org Chem. 2020;85(2):441-448. Synthesis and Photophysical Behavior of a Highly Fluorescent Family of Unsymmetrical Organoboron Complexes Containing 5-(Pyridin-2-ylmethylene)imidazolidine-2,4-dione Moieties.

Publications > Garre et al

J Org Chem. 2020, 85, 441 PubMed 31858801

Synthesis and Photophysical Behavior of a Highly Fluorescent Family of Unsymmetrical Organoboron Complexes Containing 5-(Pyridin-2-ylmethylene)imidazolidine-2,4-dione Moieties.

M Soledad Garre1, Raul Losantos2, Sara Gutierrez1, David Sucunza1, Patricia Garcia-Garcia1, Diego Sampedro2, Juan J Vaquero1

1. Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR) , Universidad de Alcala, IRYCIS , 28805 Alcala de Henares , Spain.  2. Departamento de Quimica, Centro de Investigacion en Sintesis Quimica (CISQ) , Universidad de La Rioja , Madre de Dios 53 , 26006 Logrono , Spain.

Abstract

A new and highly fluorescent family of unsymmetrical organoboron complexes containing 5-(pyridin-2-ylmethylene)imidazolidine-2,4-dione moieties has been synthesized in three steps. These compounds show strong absorptions covering a wide range of the UV-vis spectrum and are strongly emissive (varphif of up to 0.92 in CH3CN). Moreover, two fluorophores that include an alkyne or an azide group at the end of the alkyl chain and with potential utility in bioorthogonal chemistry have been developed. One of these, in which the glycol substituent provides an enhanced water solubility without compromising the fluorescence (varphif = 0.85 in water), may be of particular importance.

Noticias

J. Org. Chem. 12.2019

Synthesis and Photophysical Behavior of a Highly Fluorescent Family of Unsymmetrical Organoboron Complexes Containing 5-(Pyridin-2-ylmethylene)imidazolidine-2,4-dione Moieties

M. Soledad Garre, Raúl Losantos, Sara Gutiérrez, David Sucunza, Patricia García-García, Diego Sampedro and Juan J. Vaquero

J. Org. Chem., Article ASAP
DOI: 10.1021/acs.joc.9b02451

A new and highly fluorescent family of unsymmetrical organoboron complexes containing 5-(pyridin-2-ylmethylene)imidazolidine-2,4-dione moieties has been synthesized in three steps. These compounds show strong absorptions covering a wide range of the UV–vis spectrum and are strongly emissive (ϕf of up to 0.92 in CH3CN). Moreover, two fluorophores that include an alkyne or an azide group at the end of the alkyl chain and with potential utility in bioorthogonal chemistry have been developed. One of these, in which the glycol substituent provides an enhanced water solubility without compromising the fluorescence (ϕf = 0.85 in water), may be of particular importance.

Miembros

Rubén Manzano

Rubén Manzano San José

Assistant Professor

    • Associated Professor, Universidad de Valladolid (2022)
    • Assistant Professor, Universidad de Alcalá (2019-2022)
    • Postdoctoral researcher, Prof. J. L. Vicario group, Universidad del País Vasco (2017-2019)
    • Marie-Curie Fellowship, Prof. D. J. Dixon group, Universidad de Oxford (2015-2017)
    • Postdoctoral researcher ICIQ-IPMP, Prof. R. Martín group, ICIQ (2013-2015)
    • Postdoctoral researcher, Prof. A. S. K. Hashmi group, CaRLa-Universidad de Heidelberg (2011-2013)
    • Ph.D. Universidad de Valladolid (2010), supervisors Prof. R. Pedrosa and Prof. J. M. Andrés
    • Graduated at the Universidad de Valladolid (2005)

    I developed my PhD Thesis at the Universidad de Valladolid on the synthesis of chiral thioureas derived from amino acids and their applications as organocatalysts in enantioselective reactions of interest. Later, as postdoctoral researcher in the groups of Prof. A. S. K. Hashmi and Prof. R. Martín, I developed synthetic methodologies with gold, ruthenium, nickel and palladium catalysis. I then obtained a prestigious Marie-Curie Fellowship to carry out a project of dual enantioselective catalysis (aminocatalysis and metal catalysis with silver and copper) in the laboratories of Prof. D. J. Dixon at Oxford University. After this stage, I joined Prof. J. L. Vicario’s group at the Universidad del País Vasco as a contracted researcher, where I worked on the discovery of new reactivity patterns by enantioselective catalysis by phosphoric acids and by chiral phosphines, as well as on the synthesis of natural products. In October 2019 I joined the Universidad de Alcalá as Assistant Professor. The results of my research are collected in twenty publications, most of them with a high impact rate (ACIE (3), JACS (2), CEJ (3)…). During my research career I have supervised many students during the completion of their Master thesis and Bachelor thesis, as well as during external internships.

    • Miembros

    Clara Mañas

    Clara Mañas

    • Project associate researcher (2024)
    • Thesis defense, 04.03.2024 (“Design and study of novel reactivities of alkynylazobenzenes”)
    • Project associate researcher. Department of Organic and Inorganic Chemistry
    • Master Organic Synthesis Universidad Autónoma de Madrid (2018/2019)
    • Graduated at the Universidad Complutense de Madrid (2014-2018)

    Publicaciones en el grupo

    Visible Light-Mediated Heterodifunctionalization of Alkynylazobenzenes for 2H-Indazole Synthesis.
    Clara Mañas, Estíbaliz Merino
    Org Lett. 2024, 26, 1868
    Electrochemically driven one-pot oxidative conversion of arylhydrazines into aromatic iodides.
    Noemi Salardón, Guillermo Otárola, Clara Mañas, Estíbaliz Merino, Belen Batanero
    J. Environ. Chem. Eng. 2022, 10, 107486
    Miembros

    Julia Altarejos

    Julia Altarejos

    • Thermo Fisher Scientific 04.2024
    • Postdoctoral Researcher (2023-2024)
    • Thesis defense, 22.09.2023 (“Estudio de la reactividad del 2,2,2-trifluorodiazoetano en la síntesis de ciclopropanos y pirazoles y en la funcionalización de alcanos”)
    • Predoctoral stay, Prof. John F. Hartwig (University of California, Berkeley)
    • FPU grant Ministerio de Educación y Formación Profesional 2019-2023
    • Master Drug Discovery Universidad de Alcalá (2018/2019)
    • Graduated at the Universidad de Jaén (2014-2018)

    Publications in the group

    One-Pot (3 + 2) Cycloaddition-Isomerization-Oxidation of 2,2,2-Trifluorodiazoethane and Styryl Derivatives.
    Julia Altarejos, Estíbaliz Merino, David Sucunza, Juan J Vaquero, Javier Carreras
    J Org Chem. 2023, 88, 11258
    Synthesis of Tri- and Tetrasubstituted Alkenyl Boronates from Alkynes.
    Julia Altarejos, Antonio Valero, Rubén Manzano, Javier Carreras
    Eur. J. Chem. 2022, e202200521.
    Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates.
    Julia Altarejos, David Sucunza, Juan J Vaquero, Javier Carreras
    Org Lett. 2021 Aug 6;23(15):6174-6178. doi: 10.1021/acs.orglett.1c02420.
    Practical Solvent-Free Microwave-Assisted Hydroboration of Alkynes.
    Julia Altarejos, David Sucunza, Juan J Vaquero, Javier Carreras
    Eur. J. Org. Chem. 2020, 3024