Julia Guilleme

Universidad Autónoma de Madrid

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Trends

Author Order

Document Type

Co-Authors

Tomás Torres⊗

Universidad Autónoma de Madrid

David González‐Rodríguez

Universidad Autónoma de Madrid

Dirk M. Guldi

Friedrich-Alexander-Universität Erlangen-Nürnberg

Giulia Lavarda

Universidad Autónoma de Madrid

Giovanni Bottari

Universidad Autónoma de Madrid

Kim A. Winterfeld

Friedrich-Alexander-Universität Erlangen-Nürnberg

Michael Sekita

Friedrich-Alexander-Universität Erlangen-Nürnberg

Inés Corral

Universidad Autónoma de Madrid

Manuel Yáñez

Universidad Autónoma de Madrid

Lara Martínez‐Fernández

Consejo Superior de Investigaciones Científicas

Cooperative Institutions

Universidad Autónoma de Madrid

Madrid Institute for Advanced Studies

Friedrich-Alexander-Universität Erlangen-Nürnberg

Centre National de la Recherche Scientifique

Universidad Complutense de Madrid

Eindhoven University of Technology

IMDEA Nanoscience

University of Cambridge

Instituto de Investigaciones Químicas

Universitat de València

Author Statistics

Papers

Citation

H-Index

i-10 index

Research Field

Subphthalocyanines Axially Substituted with Electroactive Moities

Meeting abstracts/Meeting abstracts (Electrochemical Society. CD-ROM) (2018)

Tomás Torres⊗Dirk M. Guldi Giovanni Bottari Kim A. Winterfeld Giulia Lavarda

Among the molecular building blocks used for the construction of light-powered, electroactive ensembles, subphthalocyanines (SubPcs) hold a privileged position due to their outstanding photophysical properties. These singular cone-shaped, aromatic molecules show a strong absorption in the 550-650 nm region with excitation energies above 2.0 eV, high fluorescence quantum yields, a rich redox chemistry, and low reorganization energies. As part of our systematic investigation in the preparation and study of novel SubPc-based D–A systems, we decided to use 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) as partner for SubPcs. Thus, a 1,1,4,4-tetracyanobuta-1,3-diene (TCBD)-aniline moiety has been introduced, for the first time, at the axial position of two subphthalocyanines (SubPcs) peripherally substituted with hydrogen (H 12 SubPc) or fluorine atoms (F 12 SubPc). Single-crystal X-ray analysis of both SubPc-TCBD-aniline systems showed that each conjugate is a racemic mixture of two atropisomers resulting from the almost orthogonal geometry adopted by the axial TCBD unit, which were separated by chiral HPLC. Figure 1

Atropisomer

Moiety

Diene

Azulene

Fluorine

10.1149/ma2018-01/12/982

Cite

Citations (0)

Polar Switching in a Lyotropic Columnar Nematic Liquid Crystal Made of Bowl‐Shaped Molecules

Advanced Materials (2015)

Julia Guilleme Emma Cavero Teresa Sierra J. Ortega C. L. Folcia

A polar response in a lyotropic columnar nematic material is reported. The material accommodates bowl-shaped molecules with strong axial dipole moments in column segments without head-to-tail invariance. Optical second-harmonic-generation methods confirm that the nematic columns align unidirectionally under an applied electric field and the material develops remnant macroscopic polarization observable for hours. The switching takes place by a flip of the columns.

Lyotropic

Biaxial nematic

10.1002/adma.201500238

Cite

Citations (32)

CCDC 1532161: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Kim A. Winterfeld Giulia Lavarda Julia Guilleme Michael Sekita Dirk M. Guldi

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccdc.csd.cc1nfbkz

Cite

Citations (0)

CCDC 1414572: Experimental Crystal Structure Determination

The Cambridge Structural Database (2015)

Julia Guilleme Lara Martínez‐Fernández Inés Corral Manuel Yáñez David González‐Rodríguez

10.5517/cc1jgzcb

Cite

Citations (0)

Polar Self-Assembled Subphthalocyanine Columnar Stacks

Meeting abstracts/Meeting abstracts (Electrochemical Society. CD-ROM) (2015)

David González‐Rodríguez Tomás Torres⊗Julia Guilleme

Subphthalocyanines (SubPcs) are singular cone-shaped molecules with unique physicochemical properties that render them promising light-harvesting and/or donor units for photovoltaic and light-emitting applications. We were very interested in studying if such molecules could be organized in columnar stacks, both in solution and liquid-crystalline phases by hydrogen-bonding and p-p stacking interactions. The columnar aggregation of these non-planar molecules with axial dipole moments represents in itself a challenging task. Our motivation comes from the possibility of obtaining supramolecular chiral nanofibers and condensed phases that can be aligned in the presence of electric fields, yielding nanomaterials with permanent polarization and unusual ferroelectric and piezoelectric properties. Figure 1

Nanomaterials

Chemical polarity

10.1149/ma2015-01/11/997

Cite

Citations (0)

Direct Access to Axially Substituted Subphthalocyanines from Trimethylsilyl-Protected Nucleophiles

Organic Letters (2015)

Julia Guilleme Lara Martínez‐Fernández Inés Corral Manuel Yáñez David González‐Rodríguez

A new synthetic one-step approach to perform the axial ligand exchange reaction in subphthalocyanines that employs trimethylsilyl-protected nucleophiles as starting materials is reported. Theoretical calculations indicate that the exchange reaction proceeds through a similar 4-centered σ-bond metathesis transition state as the substitution with phenols. This direct method allowed us to synthesize new axial derivatives of singular importance within the chemistry of subphthalocyanines, for which the reactivity and X-ray crystalline structure were studied.

Trimethylsilyl

Reactivity

Salt metathesis reaction

10.1021/acs.orglett.5b02213

Cite

Citations (28)

CCDC 1532163: Experimental Crystal Structure Determination

The Cambridge Structural Database (2017)

Kim A. Winterfeld Giulia Lavarda Julia Guilleme Michael Sekita Dirk M. Guldi

10.5517/ccdc.csd.cc1nfbm1

Cite

Citations (0)

Subphthalocyanine–tetracyanobuta-1,3-diene–aniline conjugates: stereoisomerism and photophysical properties

Chemical Science (2019)

Kim A. Winterfeld Giulia Lavarda Julia Guilleme Dirk M. Guldi Tomás Torres⊗

Two subphthalocyanines (SubPcs) decorated at their peripheral (SubPc 1) or peripheral and axial (SubPc 2) positions with tetracyanobuta-1,3-diene (TCBD)-aniline moieties have been prepared as novel electron donor-acceptor (D-A) conjugates. In 1 and 2, the multiple functionalization of C3-symmetric SubPcs by TCBD moieties, each of them having a chiral axis, results in the formation of several stereoisomers. Variable temperature 1H-NMR studies in chlorinated solvents suggest that these latter species, which are detected at low temperatures, rapidly interconvert - on the NMR timescale - into each other at room temperature. Beside their unique structural and stereochemical features, 1 and 2 present interesting physicochemical properties. Steady-state absorption and fluorescence, as well as electrochemical studies on 1 and 2 clearly point to an important degree of electronic communication between the SubPc, the TCBD and the aniline subunits. Moreover, in both derivatives, photoexcitation of the SubPc moiety yields charge transfer products involving the electron-rich SubPc moiety and the electron-withdrawing TCBD fragment. Interestingly, such polarized excited state species evolve in 1 and 2 in different ways. While in the former compound, it directly decays to the ground state, the fourth axial TCBD moiety in 2 leads to the formation of an intermediate fully charge separated state prior to the ground state deactivation.

Moiety

Photoexcitation

Diene

10.1039/c9sc03970h

Cite

Citations (35)

Ferroelectric self-assembled molecular materials showing both rectifying and switchable conductivity

Science Advances (2017)

Andrey V. Gorbunov Miguel García‐Iglesias Julia Guilleme Tim D. Cornelissen W. S. Christian Roelofs

Combining dipolar and semiconducting functionality in a single molecule yields a ferroelectrically switchable conductivity.

Molecular Electronics

10.1126/sciadv.1701017

Cite

Citations (69)

Triflate‐Subphthalocyanines: Versatile, Reactive Intermediates for Axial Functionalization at the Boron Atom

Angewandte Chemie International Edition (2011)

Julia Guilleme David González‐Rodríguez Tomás Torres⊗

On the leave: Easily generated triflate boron subphthalocyanines are highly activated universal substrates for efficient axial substitution reactions with oxygen, sulfur, nitrogen, and carbon nucleophiles (see picture). Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

Trifluoromethanesulfonate

Nitrogen atom

Carbon fibers

Reactive intermediate

10.1002/anie.201007240

Cite

Citations (133)