Marc Villabona

Verified @gmail.com

PostDoctoral Researcher in Organic Chemistry
Friedrich Alexander Universität

Marc Villabona


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https://researchid.co/marcvp15

RESEARCH, TEACHING, or OTHER INTERESTS

Organic Chemistry
9

Scopus Publications

105

Scholar Citations

5

Scholar h-index

4

Scholar i10-index

Scopus Publications

  • Photoswitchable Active Esters for the Control of Amide Bond Formation with Light
    Marc Villabona, Arnau Marco, Rosa María Sebastián, Christopher Barner-Kowollik, Gonzalo Guirado, Jordi Hernando
    Jacs Au, 2025
    High Resolution Image Download MS PowerPoint Slide Active esters are among the most utilized reagents for (bio)materials functionalization via amide bond formation. To endow this type of ligation processes with spatiotemporal precision, we herein report the development of photoswitchable active esters, which toggle between poorly and highly reactive states upon irradiation with UV and visible light. Specifically, a dithienylethene photoswitch was introduced within the structure of common p -nitrophenyl active esters, whose electronic changes upon reversible open-closed photoisomerization turn on and off the activating effect of the p -nitro substituent on amidation reactivity. As a result, efficient light-induced modulation of amide bond formation kinetics was accomplished with these compounds, with their closed isomer exhibiting up to 24-fold enhancement of aminolysis rate with amines relative to the open state. This behavior was exploited to reach reversible light-control of illustrative examples of amidation-based ligation processes: dye labeling, polymer gelation and polymer thin film patterning, which was selectively triggered by illumination at 365 nm and inhibited by irradiation at 625 nm. These results demonstrate the potential of photoswitchable active esters to provide enhanced spatiotemporal control to the functionalization and manipulation of molecules and materials.
  • Antagonistic Two-Color Control of Polymer Network Formation
    Arnau Marco, Marc Villabona, Tugce Nur Eren, Florian Feist, Gonzalo Guirado, Rosa M. Sebastián, Jordi Hernando, Christopher Barner‐Kowollik
    Advanced Functional Materials, 2025
    Offering high spatiotemporal resolution, dual wavelength‐controlled soft matter network formation paves the way to advanced printing techniques with optimized performance. One of the most promising approaches is the antagonistic control of covalent bond‐forming reactions with two colors of light, where photoexcitation with one wavelength induces a photochemical reaction, while irradiation with the other ceases it in the presence of the first color. Herein, we combine a photoactivatable diene precursor and a photoswitchable dienophile, establishing a dual‐wavelength‐gated cycloaddition reaction capable of controlling polymer crosslinking. Upon incorporation of the diene precursor into a methacrylate copolymer and the synthesis of a difunctional dienophile cross‐linker, selective polymer network formation is promoted under sole UV illumination, while it can be efficiently suppressed with simultaneous redlight irradiation. Critically, the methodology is used for the preparation of solid polymer materials with antagonistic two‐color control of their cross‐linking status, ultimately allowing the fabrication of spatially patterned polymer films.
  • Amplified photomodulation of a bis(dithienylethene)-substituted phosphine
    Anastasiia Sherstiuk, Marc Villabona, Agustí Lledós, Jordi Hernando, Rosa María Sebastián, Evamarie Hey-Hawkins
    Dalton Transactions, 2024
    By connecting two dithienylethene photoswitches to the same phosphorus atom, amplified light-induced modulation of the electronic properties of a phosphine is achieved in situ upon photoisomerization.
  • Amplified Light-Induced pKa Modulation with Diarylethene Photoswitches
    Marc Villabona, Arnau Marco, Rosa M. Sebastián, Gonzalo Guirado, Jordi Hernando
    Journal of Organic Chemistry, 2024
    The reversible modulation of acidity using molecular photoswitches enables the remote control of a variety of (bio)chemical processes with light. Herein we investigated the structural features that allow amplifying photoinduced pKa variation in phenol-diarylethene conjugates, which toggle between low- and high-acidity states by switching the conjugation between the ionizable moiety and electron-withdrawing groups upon photoisomerization. By tuning the structure of these conjugates, high pKa modulation amplitudes were accomplished that surpass those previously reported.
  • Photo-electrochromic salt composed by viologen cation and diarylethene anion derivatives
    Hugo Cruz, Noemi Jordão, Sara Santiago, Sandra Gago, Marc Villabona, Jordi Hernando, Gonzalo Guirado, Luís C. Branco
    Electrochemical Science Advances, 2023
    A multi‐responsive photo and electrochromic salt based on a viologen derivative ([(C10)2Bpy]2+) as organic cation combined with diarylethene anion ([DTE]2−) is synthesized and characterized for the first time. The coloration of this functional salt can be modulated by light and electricity according to further applications. Photochemical determination of the quantum yields in solution for the ring‐opening and closure of [(C10)2Bpy][DTE‐COO] ionic liquid have been determined. The electrochemical and electrochromism performance have been also studied in order to evaluate the reduction of bipyridinium cation as well as the oxidation of the DTE anion in its open and closed forms. The possibility of individually addressing the redox state of the anion and cation is seen as a very attractive approach to designing photo‐electrochromic devices.
  • Dual-Wavelength Gated oxo-Diels-Alder Photoligation
    Marc Villabona, Sandra Wiedbrauk, Florian Feist, Gonzalo Guirado, Jordi Hernando, Christopher Barner-Kowollik
    Organic Letters, 2021
    The control of chemical functionalization with orthogonal light stimuli paves the way toward manipulating materials with unprecedented spatiotemporal resolution. To reach this goal, we herein introduce a photochemical reaction system that enables two-color control of covalent ligation via an oxo-Diels–Alder cycloaddition between two separate light-responsive molecular entities: a UV-activated photocaged diene based on ortho-quinodimethanes and a carbonyl dienophile appended to a diarylethene photoswitch, whose reactivity can be modulated upon illumination with UV and visible light.
  • Multistimuli-Responsive Fluorescent Switches Based on Spirocyclic Meisenheimer Compounds: Smart Molecules for the Design of Optical Probes and Electrochromic Materials
    Marc Villabona, Marina Benet, Silvia Mena, Rabih O. Al-Kaysi, Jordi Hernando, Gonzalo Guirado
    Journal of Organic Chemistry, 2018
    Fluorescent switches based on spirocyclic zwitterionic Meisenheimer (SZMC) complexes are stimuli-responsive organic molecules with application in a variety of areas. To expand their functionality, novel switching mechanisms are herein reported for these systems: (a) acid- and redox-triggered formation of an additional protonation state with distinct optical properties, and (b) solvent-induced fluorescence modulation. We demonstrate that these new features, which enable both multistimuli and multistate operation of SZMC switches, can be exploited in the preparation of smart organic materials: wide-range pH optical probes, electrochromic and electrofluorochromic films, and polymer-based fluorescent detectors of organic liquids.
  • New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
    Neus Sala, Gemma Prats, Marc Villabona, Iluminada Gallardo, Tarafah Hamdan, Rabih O. Al-Kaysi, Jordi Hernando, Gonzalo Guirado
    Dyes and Pigments, 2018
  • Fluorescent "turn-Off" detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds
    Marina Benet, Marc Villabona, Carles Llavina, Silvia Mena, Jordi Hernando, Rabih O. Al-Kaysi, Gonzalo Guirado
    Molecules, 2017
    Stable zwitterionic spirocyclic Meisenheimer compounds were synthesized using a one-step reaction between picric acid and diisopropyl (ZW1) or dicyclohexyl (ZW3) carbodiimide. A solution of these compounds displays intense orange fluorescence upon UV or visible light excitation, which can be quenched or “turned-off” by adding a mole equivalent amount of F− or CN− ions in acetonitrile. Fluorescence is not quenched in the presence of other ions such as Cl−, Br−, I−, NO2−, NO3−, or H2PO4−. These compounds can therefore be utilized as practical colorimetric and fluorescent probes for monitoring the presence of F− or CN− anions.

RECENT SCHOLAR PUBLICATIONS

  • Photoswitching of the Two‐Photon Absorption of Donor‐Acceptor Substituted Dithienylethenes
    FG Blandón‐Cumbreras, M Villabona, J Osmólska, EF Petrusevich, ...
    ChemistryEurope 3 (6), e202500072 , 2025
    2025.0
    Citations: 1
  • Photoswitchable Active Esters for the Control of Amide Bond Formation with Light
    M Villabona, A Marco, RM Sebastián, C Barner-Kowollik, G Guirado, ...
    JACS Au 5 (10), 5017-5026 , 2025
    2025.0
  • Replication Data for:" Photoswitchable Active Esters for the Control of Amide Bond Formation with Light"
    J Hernando Campos, G Guirado Lopez, M Villabona, ...
    2025.0
  • Antagonistic Two‐Color Control of Polymer Network Formation
    A Marco, M Villabona, TN Eren, F Feist, G Guirado, RM Sebastián, ...
    Advanced Functional Materials 35 (7), 2415431 , 2025
    2025.0
    Citations: 6
  • Replication Data for" Antagonistic Two-Color Control of Polymer Network Formation"
    G Guirado, J Hernando Campos, M Villabona, RM Sebastian Perez
    2025.0
  • Un nou mètode per formar materials polimèrics amb llum millorarà la resolució de la impressió 3D
    A Marco, M Villabona, GG López, RMS Pérez, JH Campos
    UAB Divulga, 0001-2 , 2025
    2025.0
  • Amplified Light-Induced p K a Modulation with Diarylethene Photoswitches
    M Villabona, A Marco, RM Sebastián, G Guirado, J Hernando
    The Journal of Organic Chemistry 89 (24), 17991-18002 , 2024
    2024.0
    Citations: 5
  • Replication Data for:" Amplified Light-Induced pKa Modulation with Diarylethene Photoswitches"
    J Hernando Campos, G Guirado Lopez, RM Sebastian, M Villabona
    2024.0
  • Replication data for" Amplified photomodulation of a bis (dithienylethene)-substituted phosphine"
    A Lledós, J Hernando Campos, M Villabona, RM Sebastian Perez
    2024.0
  • Amplified photomodulation of a bis (dithienylethene)-substituted phosphine
    A Sherstiuk, M Villabona, A Lledós, J Hernando, RM Sebastián, ...
    Dalton Transactions 53 (14), 6190-6199 , 2024
    2024.0
    Citations: 4
  • Photo‐electrochromic salt composed by viologen cation and diarylethene anion derivatives
    H Cruz, N Jordão, S Santiago, S Gago, M Villabona, J Hernando, ...
    Electrochemical Science Advances 3 (5), e2100022 , 2023
    2023.0
    Citations: 5
  • Dual-Wavelength Gated oxo -Diels–Alder Photoligation
    M Villabona, S Wiedbrauk, F Feist, G Guirado, J Hernando, ...
    Organic letters 23 (7), 2405-2410 , 2021
    2021.0
    Citations: 24
  • Multistimuli-responsive fluorescent switches based on spirocyclic meisenheimer compounds: Smart molecules for the design of optical probes and electrochromic materials
    M Villabona, M Benet, S Mena, RO Al-Kaysi, J Hernando, G Guirado
    The Journal of organic chemistry 83 (16), 9166-9177 , 2018
    2018.0
    Citations: 34
  • New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
    N Sala, G Prats, M Villabona, I Gallardo, T Hamdan, RO Al-Kaysi, ...
    Dyes and Pigments 153, 160-171 , 2018
    2018.0
    Citations: 12
  • Control de la reactivitat amb interruptors moleculars fotoinduïts
    M Villabona, G Guirado, J Hernando
    Revista de la Societat Catalana de Química, 59-73 , 2018
    2018.0
  • Fluorescent “Turn-Off” detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds
    M Benet, M Villabona, C Llavina, S Mena, J Hernando, RO Al-Kaysi, ...
    Molecules 22 (11), 1842 , 2017
    2017.0
    Citations: 14
  • Fluorescent
    M Benet, M Villabona, C Llavina, S Mena Fernández, ...

MOST CITED SCHOLAR PUBLICATIONS

  • Multistimuli-responsive fluorescent switches based on spirocyclic meisenheimer compounds: Smart molecules for the design of optical probes and electrochromic materials
    M Villabona, M Benet, S Mena, RO Al-Kaysi, J Hernando, G Guirado
    The Journal of organic chemistry 83 (16), 9166-9177 , 2018
    2018.0
    Citations: 34
  • Dual-Wavelength Gated oxo -Diels–Alder Photoligation
    M Villabona, S Wiedbrauk, F Feist, G Guirado, J Hernando, ...
    Organic letters 23 (7), 2405-2410 , 2021
    2021.0
    Citations: 24
  • Fluorescent “Turn-Off” detection of fluoride and cyanide ions using zwitterionic spirocyclic meisenheimer compounds
    M Benet, M Villabona, C Llavina, S Mena, J Hernando, RO Al-Kaysi, ...
    Molecules 22 (11), 1842 , 2017
    2017.0
    Citations: 14
  • New smart functional fluorophores based on stable spirocyclic zwitterionic Meisenheimer compounds
    N Sala, G Prats, M Villabona, I Gallardo, T Hamdan, RO Al-Kaysi, ...
    Dyes and Pigments 153, 160-171 , 2018
    2018.0
    Citations: 12
  • Antagonistic Two‐Color Control of Polymer Network Formation
    A Marco, M Villabona, TN Eren, F Feist, G Guirado, RM Sebastián, ...
    Advanced Functional Materials 35 (7), 2415431 , 2025
    2025.0
    Citations: 6
  • Amplified Light-Induced p K a Modulation with Diarylethene Photoswitches
    M Villabona, A Marco, RM Sebastián, G Guirado, J Hernando
    The Journal of Organic Chemistry 89 (24), 17991-18002 , 2024
    2024.0
    Citations: 5
  • Photo‐electrochromic salt composed by viologen cation and diarylethene anion derivatives
    H Cruz, N Jordão, S Santiago, S Gago, M Villabona, J Hernando, ...
    Electrochemical Science Advances 3 (5), e2100022 , 2023
    2023.0
    Citations: 5
  • Amplified photomodulation of a bis (dithienylethene)-substituted phosphine
    A Sherstiuk, M Villabona, A Lledós, J Hernando, RM Sebastián, ...
    Dalton Transactions 53 (14), 6190-6199 , 2024
    2024.0
    Citations: 4
  • Photoswitching of the Two‐Photon Absorption of Donor‐Acceptor Substituted Dithienylethenes
    FG Blandón‐Cumbreras, M Villabona, J Osmólska, EF Petrusevich, ...
    ChemistryEurope 3 (6), e202500072 , 2025
    2025.0
    Citations: 1
  • Photoswitchable Active Esters for the Control of Amide Bond Formation with Light
    M Villabona, A Marco, RM Sebastián, C Barner-Kowollik, G Guirado, ...
    JACS Au 5 (10), 5017-5026 , 2025
    2025.0
  • Replication Data for:" Photoswitchable Active Esters for the Control of Amide Bond Formation with Light"
    J Hernando Campos, G Guirado Lopez, M Villabona, ...
    2025.0
  • Replication Data for" Antagonistic Two-Color Control of Polymer Network Formation"
    G Guirado, J Hernando Campos, M Villabona, RM Sebastian Perez
    2025.0
  • Un nou mètode per formar materials polimèrics amb llum millorarà la resolució de la impressió 3D
    A Marco, M Villabona, GG López, RMS Pérez, JH Campos
    UAB Divulga, 0001-2 , 2025
    2025.0
  • Replication Data for:" Amplified Light-Induced pKa Modulation with Diarylethene Photoswitches"
    J Hernando Campos, G Guirado Lopez, RM Sebastian, M Villabona
    2024.0
  • Replication data for" Amplified photomodulation of a bis (dithienylethene)-substituted phosphine"
    A Lledós, J Hernando Campos, M Villabona, RM Sebastian Perez
    2024.0
  • Control de la reactivitat amb interruptors moleculars fotoinduïts
    M Villabona, G Guirado, J Hernando
    Revista de la Societat Catalana de Química, 59-73 , 2018
    2018.0
  • Fluorescent
    M Benet, M Villabona, C Llavina, S Mena Fernández, ...