Hexabenzocoronene–Benzimidazole Hybrid Architectures and Faraday Rotation of the First Hexabenzocoronene–Phthalocyanine

Rocha Ortiz A, Suleymanov AA, Puhlmann P, Krischer D, Müller C, Zahn D, Swager TM, Hirsch A (2025)

Publication Type: Journal article

Publication year: 2025

Journal

Article Number: e22494

DOI: 10.1002/anie.202522494

Abstract

The synthesis and characterization of a first example of a Ni-phthalocyanine (Pc) hybrid molecule carrying four hexa-peri-hexabenzocoronene (HBC) substituents and of three HBC-benzimidazole derivatives is reported. These π-electron rich chromophores exhibit a high molar absorption coefficient with extended absorption up to 460 nm. Particularly, HBC-Pc absorbs throughout most of the UV–vis range with the Pc Q-band located at 672 nm. This enables its investigation as a Faraday rotator where it displayed a remarkable Verdet constant of −1.4 × 105 deg T−1m−1 at 700 nm assigned to Faraday A-term activity. Electrochemical measurements supported by DFT calculations elucidated the electronic structure of the molecules together with excited state molecular orbital analysis using TDDFT. Here, HBC-Pc showed a HOMO/LUMO gap considerably lower than the other HBC-based compounds due to the introduction of the Pc scaffold.

Authors with CRIS profile

Involved external institutions

Massachusetts Institute of Technology (MIT) United States (USA) (US)

How to cite

APA:

Rocha Ortiz, A., Suleymanov, A.A., Puhlmann, P., Krischer, D., Müller, C., Zahn, D.,... Hirsch, A. (2025). Hexabenzocoronene–Benzimidazole Hybrid Architectures and Faraday Rotation of the First Hexabenzocoronene–Phthalocyanine. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202522494

MLA:

Rocha Ortiz, Antonia, et al. "Hexabenzocoronene–Benzimidazole Hybrid Architectures and Faraday Rotation of the First Hexabenzocoronene–Phthalocyanine." Angewandte Chemie International Edition (2025).

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