Communication
Induced Self‐Assembly of a Tetrathiafulvalene‐Based Open‐Shell Dyad through Intramolecular Electron Transfer†
†
This work was supported by the DGI grant POMAs (grant number CTQ2010‐19501), the Networking Research Center on Bioengineering, Biomaterials, and Nanomedicine (CIBER‐BBN), and the Generalitat de Catalunya (grant number 2009SGR00516). J.G. is grateful to the CSIC for a “JAE‐Doc” fellowship.
Abstract
An organic switch : An open‐shell dyad, consisting of an electron acceptor perchlorotriphenylmethyl radical unit linked to an electron π‐donor tetrathiafulvalene unit through a vinylene π‐bridge, was synthesized (see picture). The self‐assembly of the dyad in solution induced by its intramolecular electron transfer was studied.
Citing Literature
Number of times cited according to CrossRef: 35
- Olivier Cador, Boris Le Guennic, Lahcène Ouahab, Fabrice Pointillart, Decorated Tetrathiafulvalene‐Based Ligands: Powerful Chemical Tools for the Design of Single‐Molecule Magnets, European Journal of Inorganic Chemistry, 10.1002/ejic.201900981, 2020, 2, (148-164), (2019).
- Judith Guasch, Núria Crivillers, Manuel Souto, Imma Ratera, Concepció Rovira, Paolo Samorì, Jaume Veciana, Two-dimensional self-assembly and electrical properties of the donor-acceptor tetrathiafulvalene-polychlorotriphenylmethyl radical on graphite substrates, Journal of Applied Physics, 10.1063/1.5065448, 125, 14, (142909), (2019).
- Tsuyoshi Murata, Kazuki Kariyazono, Shusaku Ukai, Akira Ueda, Yuki Kanzaki, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Yasushi Morita, Trioxotriangulene with carbazole: a donor–acceptor molecule showing strong near-infrared absorption exceeding 1000 nm, Organic Chemistry Frontiers, 10.1039/C9QO00663J, (2019).
- Keishiro Tahara, Nazuna Terashita, Ken Tokunaga, Shiomi Yabumoto, Jun‐ichi Kikuchi, Yoshiki Ozawa, Masaaki Abe, Zwitterionic Mixed Valence: Internalizing Counteranions into a Biferrocenium Framework toward Molecular Expression of Half‐Cells in Quantum Cellular Automata, Chemistry – A European Journal, 10.1002/chem.201902840, 25, 60, (13728-13738), (2019).
- Manuel Souto, Valentin Díez-Cabanes, Li Yuan, Adriana R. Kyvik, Imma Ratera, Christian A. Nijhuis, Jerome Cornil, Jaume Veciana, Influence of the donor unit on the rectification ratio in tunnel junctions based on donor–acceptor SAMs using PTM units as acceptors, Physical Chemistry Chemical Physics, 10.1039/C8CP05488F, (2018).
- Katsuya Sako, Tomoya Hasegawa, Hiroyuki Onda, Michito Shiotsuka, Motonori Watanabe, Teruo Shinmyozu, Sachiko Tojo, Mamoru Fujitsuka, Tetsuro Majima, Yasukazu Hirao, Takashi Kubo, Tetsuo Iwanaga, Shinji Toyota, Hiroyuki Takemura, Donor–Donor′–Acceptor Triads Based on [3.3]Paracyclophane with a 1,4‐Dithiafulvene Donor and a Cyanomethylene Acceptor: Synthesis, Structure, and Electrochemical and Photophysical Properties, Chemistry – A European Journal, 10.1002/chem.201801774, 24, 44, (11407-11416), (2018).
- Manuel Souto, Maria Chiara Gullo, HengBo Cui, Nicola Casati, Fabio Montisci, Harald O. Jeschke, Roser Valentí, Imma Ratera, Concepció Rovira, Jaume Veciana, Role of the Open‐Shell Character on the Pressure‐Induced Conductivity of an Organic Donor–Acceptor Radical Dyad, Chemistry – A European Journal, 10.1002/chem.201800881, 24, 21, (5500-5505), (2018).
- Yury A. Ten, Oleg G. Salnikov, Svetlana A. Amitina, Dmitri V. Stass, Tatyana V. Rybalova, Maxim S. Kazantsev, Artem S. Bogomyakov, Evgeny A. Mostovich, Dmitrii G. Mazhukin, The Suzuki–Miyaura reaction as a tool for modification of phenoxyl-nitroxyl radicals of the 4 H -imidazole N -oxide series , RSC Advances, 10.1039/C8RA05103H, 8, 46, (26099-26107), (2018).
- Xiaojin Wu, Jun Oh Kim, Samara Medina, Francisco J. Ramírez, Paula Mayorga Burrezo, Shaofei Wu, Zheng Long Lim, Christoph Lambert, Juan Casado, Dongho Kim, Jishan Wu, Push–Pull‐Type Polychlorotriphenylmethyl Radicals: New Two‐Photon Absorbers and Dyes for Generation of Photo‐Charges, Chemistry – A European Journal, 10.1002/chem.201701875, 23, 32, (7698-7702), (2017).
- Manuel Souto, Joaquín Calbo, Imma Ratera, Enrique Ortí, Jaume Veciana, Tetrathiafulvalene–Polychlorotriphenylmethyl Dyads: Influence of Bridge and Open‐Shell Characteristics on Linear and Nonlinear Optical Properties, Chemistry – A European Journal, 10.1002/chem.201701623, 23, 46, (11067-11075), (2017).
- Jun Yoshida, Kyohei Kuwahara, Kota Suzuki, Hidetaka Yuge, Long-Range Intramolecular Electronic Communication in a Trinuclear Ruthenium Tropolonate Complex, Inorganic Chemistry, 10.1021/acs.inorgchem.6b02249, 56, 4, (1846-1856), (2017).
- Davide Blasi, Domna M. Nikolaidou, Francesca Terenziani, Imma Ratera, Jaume Veciana, Excimers from stable and persistent supramolecular radical-pairs in red/NIR-emitting organic nanoparticles and polymeric films, Physical Chemistry Chemical Physics, 10.1039/C7CP00623C, 19, 13, (9313-9319), (2017).
- Manuel Souto, Concepció Rovira, Imma Ratera, Jaume Veciana, TTF–PTM dyads: from switched molecular self assembly in solution to radical conductors in solid state, CrystEngComm, 10.1039/C6CE01660J, 19, 2, (197-206), (2017).
- Bin Yao, Yue Zhou, Xichong Ye, Rong Wang, Jie Zhang, Xinhua Wan, A Star-Shaped Molecule with Low-Lying Lowest Unoccupied Molecular Orbital Level, n-Type Panchromatic Electrochromism, and Long-Term Stability, Organic Letters, 10.1021/acs.orglett.7b00522, 19, 8, (1990-1993), (2017).
- Haiet Douib, Marin Puget, Yan Suffren, Fabrice Pointillart, Kevin Bernot, Boris Le Guennic, Olivier Cador, Abdelkrim Gouasmia, Lahcène Ouahab, Photo-physical properties of donor-acceptor-radical triad based on functionalized tetrathiafulvalene and nitronyl nitroxide radical, Dyes and Pigments, 10.1016/j.dyepig.2017.06.010, 145, (285-293), (2017).
- Manuel Souto, HengBo Cui, Miriam Peña-Álvarez, Valentín G. Baonza, Harald O. Jeschke, Milan Tomic, Roser Valentí, Davide Blasi, Imma Ratera, Concepció Rovira, Jaume Veciana, Pressure-Induced Conductivity in a Neutral Nonplanar Spin-Localized Radical, Journal of the American Chemical Society, 10.1021/jacs.6b02888, 138, 36, (11517-11525), (2016).
- Flavia Pop, Narcis Avarvari, Covalent non-fused tetrathiafulvalene–acceptor systems, Chem. Commun., 10.1039/C6CC01827K, 52, 51, (7906-7927), (2016).
- Francesco Di Maiolo, Cristina Sissa, Anna Painelli, Combining intra- and intermolecular charge-transfer: a new strategy towards molecular ferromagnets and multiferroics, Scientific Reports, 10.1038/srep19682, 6, 1, (2016).
- Manuel Souto, Vega Lloveras, Sergi Vela, Maria Fumanal, Imma Ratera, Jaume Veciana, Three Redox States of a Diradical Acceptor–Donor–Acceptor Triad: Gating the Magnetic Coupling and the Electron Delocalization, The Journal of Physical Chemistry Letters, 10.1021/acs.jpclett.6b00912, 7, 12, (2234-2239), (2016).
- Manuel Souto, Dan Bendixen, Morten Jensen, Valentín Díez-Cabanes, Jérôme Cornil, Jan Jeppesen, Imma Ratera, Concepció Rovira, Jaume Veciana, Synthesis and Characterization of Ethylenedithio-MPTTF-PTM Radical Dyad as a Potential Neutral Radical Conductor, Magnetochemistry, 10.3390/magnetochemistry2040046, 2, 4, (46), (2016).
- Manuel Souto, Marta V. Solano, Morten Jensen, Dan Bendixen, Francesca Delchiaro, Alberto Girlando, Anna Painelli, Jan O. Jeppesen, Concepció Rovira, Imma Ratera, Jaume Veciana, Self‐Assembled Architectures with Segregated Donor and Acceptor Units of a Dyad Based on a Monopyrrolo‐Annulated TTF–PTM Radical, Chemistry – A European Journal, 10.1002/chem.201500497, 21, 24, (8816-8825), (2015).
- Shinsuke Nishida, Yasushi Morita, Air‐Stable Redox‐Active Neutral Radicals, Organic Redox Systems, 10.1002/9781118858981, (177-243), (2015).
- A. Y. Tesio, D. Blasi, M. Olivares-Marín, I. Ratera, D. Tonti, J. Veciana, Organic radicals for the enhancement of oxygen reduction reaction in Li–O 2 batteries , Chemical Communications, 10.1039/C5CC07242E, 51, 99, (17623-17626), (2015).
- Francesco Romano, Roberta Manoni, Paola Franchi, Elisabetta Mezzina, Marco Lucarini, Supramolecular Control of Spin Exchange in a Spin‐Labelled [2]Rotaxane Incorporating a Tetrathiafulvalene Unit, Chemistry – A European Journal, 10.1002/chem.201406301, 21, 7, (2775-2779), (2014).
- Manuel Souto, Dayana C. Morales, Judith Guasch, Imma Ratera, Concepció Rovira, Anna Painelli, Jaume Veciana, Intramolecular electron transfer and charge delocalization in bistable donor–acceptor systems based on perchlorotriphenylmethyl radicals linked to ferrocene and tetrathiafulvalene units, Journal of Physical Organic Chemistry, 10.1002/poc.3296, 27, 6, (465-469), (2014).
- Marçal Capdevila-Cortada, Jordi Ribas-Arino, Juan J. Novoa, Assessing the Performance of CASPT2 and DFT Methods for the Description of Long, Multicenter Bonding in Dimers between Radical Ions, Journal of Chemical Theory and Computation, 10.1021/ct4010257, 10, 2, (650-658), (2014).
- Lluís Fajarí, Robert Papoular, Marta Reig, Enric Brillas, José Luis Jorda, Oriol Vallcorba, Jordi Rius, Dolores Velasco, Luis Juliá, Charge Transfer States in Stable Neutral and Oxidized Radical Adducts from Carbazole Derivatives, The Journal of Organic Chemistry, 10.1021/jo4028215, 79, 4, (1771-1777), (2014).
- Shinsuke Nishida, Kozo Fukui, Yasushi Morita, Hydrogen‐Bonding Effect on Spin‐Center Transfer of Tetrathiafulvalene‐Linked 6‐Oxophenalenoxyl Evaluated Using Temperature‐Dependent Cyclic Voltammetry and Theoretical Calculations, Chemistry – An Asian Journal, 10.1002/asia.201301188, 9, 2, (500-505), (2013).
- Judith Guasch, Xavier Fontrodona, Imma Ratera, Concepció Rovira, Jaume Veciana, The perchlorotriphenylmethyl (PTM) radical, Acta Crystallographica Section C, 10.1107/S0108270113002072, 69, 3, (255-257), (2013).
- IUPAC 2013 Distinguished Women in Chemistry or Chemical Engineering / New Members of the Royal Swedish Academy of Sciences, Angewandte Chemie International Edition, 10.1002/anie.201305827, 52, 39, (10154-10155), (2013).
- IUPAC 2013 Distinguished Women in Chemistry or Chemical Engineering / Neue Mitglieder der königlichen schwedischen Akademie der Wissenschaften, Angewandte Chemie, 10.1002/ange.201305827, 125, 39, (10340-10341), (2013).
- Judith Guasch, Luca Grisanti, Manuel Souto, Vega Lloveras, José Vidal-Gancedo, Imma Ratera, Anna Painelli, Concepció Rovira, Jaume Veciana, Intra- and Intermolecular Charge Transfer in Aggregates of Tetrathiafulvalene-Triphenylmethyl Radical Derivatives in Solution, Journal of the American Chemical Society, 10.1021/ja400281b, 135, 18, (6958-6967), (2013).
- Judith Guasch, Luca Grisanti, Stefan Jung, Dayana Morales, Gabriele D’Avino, Manuel Souto, Xavier Fontrodona, Anna Painelli, Franz Renz, Imma Ratera, Jaume Veciana, Bistability of Fc-PTM-Based Dyads: The Role of the Donor Strength, Chemistry of Materials, 10.1021/cm400147p, 25, 5, (808-814), (2013).
- R. Alan Aitken, Lynn A. Power, Five-Membered Ring Systems, , 10.1016/B978-0-08-099406-2.00011-X, (277-289), (2013).
- Manuel Souto, Judith Guasch, Vega Lloveras, Paula Mayorga, Juan T. López Navarrete, Juan Casado, Imma Ratera, Concepció Rovira, Anna Painelli, Jaume Veciana, Thermomagnetic Molecular System Based on TTF-PTM Radical: Switching the Spin and Charge Delocalization, The Journal of Physical Chemistry Letters, 10.1021/jz4013855, 4, 16, (2721-2726), (2013).
