Quadrupolar Cyclopenta[hi]aceanthrylene-Based Electron Donor-Acceptor-Donor Conjugates: Charge Transfer versus Charge Separation

Schierl C, Alex W, Mateo LM, Ballesteros B, Shimizu D, Osuka A, Torres T, Guldi DM, Bottari G (2019)

Publication Type: Journal article

Publication year: 2019

Journal

Angewandte Chemie International Edition Wiley

DOI: 10.1002/anie.201906206

Abstract

Cyclopenta[hi]aceanthrylenes (CPAs) have been functionalized at two of the peripheral positions with electronically inert trimethylsilylethynyl (1), as well as with electron-donating 4-ethynyl-N,N-dimethylaniline (2), ethynyl ZnIIphthalocyanine (3), and ethynyl ZnIIporphyrin (4) units. Consistent with X-ray crystal structures of 2 and 4, analyses of absorption and fluorescence of 2–4 point to strong electronic communication between the CPA and the peripheral units, affording quadrupolar electron donor-acceptor-donor charge-transfer conjugates. By virtue of their quadrupolar/dipolar charge-transfer characters in the excited state, 2–4 exhibit fluoro-solvatochromism. Transient absorption spectroscopy confirmed delocalized quadrupolar ground states and formation of weakly solvent stabilized quadrupolar singlet excited states. The latter transform into strongly stabilized dipolar excited states before deactivating to the ground state in 2 and give rise to a fully charge separated state in 3 and 4.

Authors with CRIS profile

Christoph Schierl Lehrstuhl für Physikalische Chemie I Wiebke Alex Lehrstuhl für Physikalische Chemie I Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Universidad Autónoma de Madrid (UAM) ES Spain (ES) Kyoto University / 京都大学 Kyōto daigaku JP Japan (JP)

How to cite

APA:

Schierl, C., Alex, W., Mateo, L.M., Ballesteros, B., Shimizu, D., Osuka, A.,... Bottari, G. (2019). Quadrupolar Cyclopenta[hi]aceanthrylene-Based Electron Donor-Acceptor-Donor Conjugates: Charge Transfer versus Charge Separation. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201906206

MLA:

Schierl, Christoph, et al. "Quadrupolar Cyclopenta[hi]aceanthrylene-Based Electron Donor-Acceptor-Donor Conjugates: Charge Transfer versus Charge Separation." Angewandte Chemie International Edition (2019).

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