Thionated naphthalene diimides: tuneable chromophores for applications in photoactive dyads

Pearce, Nicholas; Davies, E. Stephen; Horvath, Raphael; Pfeiffer, Constance R.; Sun, Xue-Xhong; Lewis, William; McMaster, Jonathan; George, Michael W.; Champness, Neil R.

Abstract

Varying the degree of thionation of a series of naphthalene diimide (NDI) and naphthalic imides (NI) phenothiazine dyad systems afford a systematic approach for tuning of the system’s donor-acceptor energy gap. Each dyad was compared to model NDI/NI systems and fully characterised through single crystal X-ray diffraction, NMR, cyclic voltammetry, electron paramagnetic resonance (EPR), transient absorption spectroscopy (TA), time-resolved infra-red spectroscopy (TRIR) and DFT. The measurements reveal that thionation increases both electron affinity of the NDI/NI acceptor dyad component and accessibility of the singly or doubly reduced states. Furthermore, FTIR and TA measurements show that excited state behaviour is greatly affected by thionation of the NDI and induces a decrease in the lifetime of the excited states formed upon the creation of charge-separated states.

Citation

Pearce, N., Davies, E. S., Horvath, R., Pfeiffer, C. R., Sun, X.-X., Lewis, W., McMaster, J., George, M. W., & Champness, N. R. (2018). Thionated naphthalene diimides: tuneable chromophores for applications in photoactive dyads. Physical Chemistry Chemical Physics, 20(2), https://doi.org/10.1039/c7cp06952a

• Journal Article Type: Article
• Acceptance Date: Nov 6, 2017
• Online Publication Date: Nov 6, 2017
• Publication Date: Jan 14, 2018
• Deposit Date: Feb 26, 2018
• Publicly Available Date: Nov 7, 2018
• Journal: Physical Chemistry Chemical Physics
• Print ISSN: 1463-9076
• Electronic ISSN: 1463-9084
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 20
• Issue: 2
• DOI: https://doi.org/10.1039/c7cp06952a
• Public URL: https://nottingham-repository.worktribe.com/output/904955
• Publisher URL: http://pubs.rsc.org/en/content/articlelanding/2018/cp/c7cp06952a#!divAbstract
• Contract Date: Feb 26, 2018