Intense Ground-State Charge-Transfer Interactions in Low-Bandgap, Panchromatic Phthalocyanine-Tetracyanobuta-1,3-diene Conjugates

Sekita M, Ballesteros B, Diederich F, Guldi DM, Bottari G, Torres T (2016)

Publication Type: Journal article

Publication year: 2016

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 55

Pages Range: 5560-5564

Journal Issue: 18

DOI: 10.1002/anie.201601258

Abstract

A cycloaddition-retroelectrocyclization reaction between tetracyanoethylene and two zinc phthalocyanines (ZnIIPcs) bearing one or four anilino-substituted alkynes has been used to install a strong, electron-accepting tetracyanobuta-1,3-diene (TCBD) between the electron-rich ZnIIPc and aniline moieties. A combination of photophysical, electrochemical, and spectroelectrochemical investigations with the ZnIIPc-TCBD-aniline conjugates, which present panchromatic absorptions in the visible region extending all the way to the near infrared, show that the formal replacement of the triple bond by TCBD has a dramatic effect on their ground- and excited-state features. In particular, the formation of extremely intense, ground-state charge-transfer interactions between ZnIIPc and the electron-accepting TCBD were observed, something unprecedented not only in Pc chemistry but also in TCBD-based porphyrinoid systems.

Authors with CRIS profile

Michael Sekita Sonderforschungsbereich 953/3 Synthetische Kohlenstoffallotrope Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Universidad Autónoma de Madrid (UAM) ES Spain (ES) Eidgenössische Technische Hochschule Zürich (ETHZ) / Swiss Federal Institute of Technology in Zurich CH Switzerland (CH)

How to cite

APA:

Sekita, M., Ballesteros, B., Diederich, F., Guldi, D.M., Bottari, G., & Torres, T. (2016). Intense Ground-State Charge-Transfer Interactions in Low-Bandgap, Panchromatic Phthalocyanine-Tetracyanobuta-1,3-diene Conjugates. Angewandte Chemie International Edition, 55(18), 5560-5564. https://doi.org/10.1002/anie.201601258

MLA:

Sekita, Michael, et al. "Intense Ground-State Charge-Transfer Interactions in Low-Bandgap, Panchromatic Phthalocyanine-Tetracyanobuta-1,3-diene Conjugates." Angewandte Chemie International Edition 55.18 (2016): 5560-5564.

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