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Influence of $β$ -octabromination on free-base triarylcorroles: Electrochemistry and protonation-deprotonation reactions in nonaqueous media

Yang Song

Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA

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Yuanyuan Fang

Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA

School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China

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Zhongping Ou

Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA

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Jan Capar

Department of Chemistry and Center for Theoretical and Computational Chemistry, University of Tromsø, 9037 Tromsø, Norway

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Chenyi Wang

Department of Chemistry, Portland State University, Portland, Oregon 97207-0751, USA

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Jeanet Conradie

Department of Chemistry, University of the Free State, 9300 Bloemfontein, South Africa

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Kolle E. Thomas

Department of Chemistry and Center for Theoretical and Computational Chemistry, University of Tromsø, 9037 Tromsø, Norway

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Carl C. Wamser

Department of Chemistry, Portland State University, Portland, Oregon 97207-0751, USA

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Abhik Ghosh

Department of Chemistry and Center for Theoretical and Computational Chemistry, University of Tromsø, 9037 Tromsø, Norway

E-mail Address: [email protected]

Corresponding authors.

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and

Karl M. Kadish

Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA

E-mail Address: [email protected]

Corresponding authors.

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https://doi.org/10.1142/S1088424617500602Cited by:2

Abstract

Electrochemical and acid-base properties of four free-base triarylcorroles were examined in nonaqueous media. These compounds are represented here as (tdcc)H $_{3}$ , (tpfc)H $_{3}$ , (Br $_{8}$ tdcc)H $_{3}$ and (Br $_{8}$ tpfc)H $_{3}$ , where tdcc and tpfc are the trianions of tris(2,6-dichlorophenyl)corrole and tris(pentafluorophenyl)corrole, respectively. Different spectroscopic and electrochemical properties were observed for the $β$ -brominated corroles as compared to the non-brominated derivatives, due in part to the corrole ring distortion and in part to the strong electron-withdrawing properties of the Br groups. The brominated free-base corroles are easier to deprotonate than the non-brominated corroles in solution, which was confirmed by electrochemistry and spectroelectrochemistry as well as protonation/deprotonation reactions of the compounds with acid or base in PhCN. The electrochemistry of the protonated and deprotonated corroles is presented and comparisons made with previously published data for other protonated and deprotonated free-base corroles under the same solution conditions.

Keywords:

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Received 18 July 2017

Accepted 17 October 2017

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Influence of β-octabromination on free-base triarylcorroles: Electrochemistry and protonation-deprotonation reactions in nonaqueous media

Abstract

References

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Influence of $β$ -octabromination on free-base triarylcorroles: Electrochemistry and protonation-deprotonation reactions in nonaqueous media