Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• acetylenic scaffolds comprised of enediyne units are known to behave as good electron acceptors [15][16], and we became interested in combining the IF-DTF scaffold with such motifs to generate novel multi-redox systems. For example, the radiaannulene moiety RA shown in Figure 1 (or its truncated counterpart

• can be adjusted by several hundreds of millivolts for donor–acceptor IF scaffolds. Introduction of both the dithiafulvene and radiaannulene units along the indenofluorene scaffold provided a donor–acceptor compound covering a particularly broad absorption profile and with a redshifted longest

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

• Huixin Jiang,
• Virginia Mazzanti,
• Christian R. Parker,
• Søren Lindbæk Broman,
• Jens Heide Wallberg,
• Karol Lušpai,
• Adam Brincko,
• Henrik G. Kjaergaard,
• Anders Kadziola,
• Peter Rapta,
• Ole Hammerich and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

• were investigated by cyclic voltammetry, UV–vis–NIR and EPR absorption spectroscopical methods of the electrochemically generated oxidized species. The electron-accepting properties of the acetylenic cores were also investigated electrochemically. Keywords: alkynes; mixed valence; radiaannulene

• structure, as in the radiaannulene 2a, communication between the two TTFs is observed in the cyclic voltammetry experiment, and the first two-electron event showed the waves diverging from each other (two stepwise oxidations) [10]. In addition, the intermediate radical cation showed an IVCT absorption at

• compound 7 also connects two TTFs in a cross-conjugated pathway. The synthesis of radiaannulene 2b was very recently described [15], and the properties of 2a and 2b are included here for comparison to those of the new unsymmetrical radiaannulene 8 that has a cross-conjugated TEE-diyl and a linearly