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Charge-Gating Dibenzothiophene-S,S-dioxide Bridges in Electron Donor–Bridge–Acceptor Conjugates

Yzambart, Gilles; Zieleniewska, Anna; Bauroth, Stefan; Clark, Timothy; Bryce, Martin R.; Guldi, Dirk M.

Charge-Gating Dibenzothiophene-S,S-dioxide Bridges in Electron Donor–Bridge–Acceptor Conjugates Thumbnail


Gilles Yzambart

Anna Zieleniewska

Stefan Bauroth

Timothy Clark

Dirk M. Guldi


The synthesis of a series of new electron donor–bridge–acceptor (D–B–A) conjugates (18–20) comprising electron-donating zinc(II) porphyrins (ZnPs) and electron-accepting fullerenes (C60s) connected through various co-oligomer bridges containing both dibenzothiophene-S,S-dioxide and fluorene units is reported. Detailed investigations using cyclic voltammetry, absorption, fluorescence, and femto/nanosecond transient absorption spectroscopy in combination with quantum chemical calculations have enabled us to develop a detailed mechanistic view of the charge-transfer processes that follow photoexcitation of ZnP, the bridge, or C60. Variations in the dynamics of charge separation, charge recombination, and charge-transfer gating are primarily consequences of the electronic properties of the co-oligomer bridges, including their electron affinity and the energy levels of the excited states. In particular, placing one dibenzothiophene-S,S-dioxide building block at the center of the molecular bridge flanked by two fluorene building blocks, as in 20, favors hole rather than electron transfer between the remote electron donors and acceptors, as demonstrated by exciting C60 rather than ZnP. In 18 and 19, in which one dibenzothiophene-S,S-dioxide and one fluorene building block constitute the molecular bridge, photoexcitation of either ZnP or C60 results in both hole and electron transfer. Dibenzothiophene-S,S-dioxide is thus shown to be an excellent building block for probing how subtle structural and electronic variations in the bridge affect unidirectional charge transport in D–B–A conjugates. The experimental results are supported by computational calculations.


Yzambart, G., Zieleniewska, A., Bauroth, S., Clark, T., Bryce, M. R., & Guldi, D. M. (2017). Charge-Gating Dibenzothiophene-S,S-dioxide Bridges in Electron Donor–Bridge–Acceptor Conjugates. Journal of Physical Chemistry C,

Journal Article Type Article
Acceptance Date May 31, 2017
Online Publication Date Jun 19, 2017
Publication Date Jun 19, 2017
Deposit Date Jun 20, 2017
Publicly Available Date Jun 19, 2018
Journal Journal of Physical Chemistry C
Print ISSN 1932-7447
Electronic ISSN 1932-7455
Publisher American Chemical Society
Peer Reviewed Peer Reviewed


Accepted Journal Article (2.8 Mb)

Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The journal of physical chemistry C, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see

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