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http://hdl.handle.net/1942/35431
Title: | Heavy-Atom-Free Bay-Substituted Perylene Diimide Donor-Acceptor Photosensitizers | Authors: | DECKERS, Jasper CARDEYNAELS, Tom LUTSEN, Laurence Champagne, Benoît MAES, Wouter |
Issue Date: | 2021 | Publisher: | WILEY-V C H VERLAG GMBH | Source: | ChemPhysChem (Print), 22 (14) , p. 1488 -1496 | Abstract: | Perylene diimide (PDI) dyes are extensively investigated because of their favorable photophysical characteristics for a wide range of organic material applications. Fine-tuning of the optoelectronic properties is readily achieved by functionaliza-tion of the electron-deficient PDI scaffold. Here, we present four new donor-acceptor type dyads, wherein the electron donor units-benzo[1,2-b : 4,5-b']dithiophene, 9,9-dimethyl-9,10-dihy-droacridine, dithieno[3,2-b : 2',3'-d]pyrrole, and triphenylamine-are attached to the bay-positions of the PDI acceptor. Intersystem crossing occurs for these systems upon photo-excitation, without the aid of heavy atoms, resulting in singlet oxygen quantum yields up to 80 % in toluene solution. Furthermore, this feature is retained when the system is directly irradiated with energy corresponding to the intramolecular charge-transfer absorption band (at 639 nm). Geometrical optimization and (time-dependent) density functional theory calculations afford more insights into the requirements for intersystem crossing such as spin-orbit coupling, dihedral angles, the involvement of charge-transfer states, and energy level alignment. | Keywords: | charge transfer;intersystem crossing;perylene diimides;photosensitizers;singlet oxygen | Document URI: | http://hdl.handle.net/1942/35431 | ISSN: | 1439-4235 | e-ISSN: | 1439-7641 | DOI: | 10.1002/cphc.202100269 | ISI #: | WOS:000661498700001 | Rights: | 2021 Wiley-VCH GmbH | Category: | A1 | Type: | Journal Contribution | Validations: | ecoom 2022 |
Appears in Collections: | Research publications |
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File | Description | Size | Format | |
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cphc.202100269.pdf Restricted Access | Published version | 1.36 MB | Adobe PDF | View/Open Request a copy |
Manuscript revised.pdf | Peer-reviewed author version | 821 kB | Adobe PDF | View/Open |
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