DoSChem awards with 24811.20 Euro the joint expertise of Martina Crosta (Institute of Organic Chemistry, Davide Bonifazi group) and David Hernández-Castillo (Institute for Theoretical Chemistry, Leticia González group) with the proposal “Conjugation-Induced TADF Emitters: A Theoretically-Driven Experimental Design”. Good luck Martina and David with their project!
At the European-Winter School on Physical Organic Chemistry (E-WISPOC 23, https://www.ewispoc.com/) that took place in Bressasone between February 5-10, Rúben Ferreira was awarded with the best flash talk award for his poster with the title “Dynamic Covalent Photowriting“ Congratulations to your prize!
The “IrrevoChrom” project is one out of total eleven recently granted FFG spin-off fellowships that will be led by FFG fellow Laura Maggini and host Davide Bonifazi at the Institute of Organic Chemistry, University of Vienna. The FFG-funded IrrevoChrom Spin-off Fellowship will build on the patent developed in the Bonifazi group (EP application No EP22164076.6) within the framework of the Charisma Marie-Sklodowska Curie project they are coordinating, entailing the formulation of an irreversible EC matrix composed of both the chromogenic material, an anti-oxidant and electrolyte, to develop and scale-up a commercially viable and completely irreversible electrochromic ink compatible with industrial manufacturing processes. Upon activation, this ink will provide a stark and permanent color transition (colorless to black), impossible to reverse. Thanks to the new formulations developed in this Fellowship, we will match our technology with industrial ECDs productions processes, jump starting its commercial exploitation, and develop in collaboration with Silicon Austria Labs activatable tamperproof demos.
Organic electrochromic materials change colour with an electric current and have many applications as low energy visual indicators. Based on the innovative, sustainable and irreversible electrochromic (EC) materials developed in the group of Davide Bonifazi (Institute of Organic Chemistry) and patented (EP Nº EP22164076.6), this funding will enable the developement of chemically-ensured high-security tickets and labels. The innovative chemically-ensured high-security tickets and labels comprise an EC display affording unequivocal, irreversible and tamperproof color change upon secure activation. This affordable, additive manufacturing-compatible and easy to read out technology will prove very valuable in fighting counterfeiting from smaller to large-scale events. The project entitled “High-security irreversible electrochromic tickets prototype development” will be led by Laura Maggini and hosted by group leader Davide Bonifazi, and started at the beginning of December (until July 31st, 2023).
Franceschini, M., Crosta, M., Ferreira, R. R., Poletto, D., Demitri, N., Zobel, J. P., González, L., and Bonifazi, D. J. Am. Chem. Soc. 2022, 144, 47, 21470-21484 doi: 10.1021/jacs.2c06803 Abstract: Here, we report the synthesis of BN-doped graphenoid nanoribbons, in which peripheral carbon atoms at the zigzag edges have been selectively replaced by boron and nitrogen atoms as BN and NBN motifs. This includes high-yielding ring closure key steps that, through N-directed borylation reaction using solely BBr3, allow the planarization of meta-oligoarylenyl precursors, through the formation of B–N and B–C bonds, to give ter-, quater-, quinque-, and sexi-arylenyl nanoribbons. X-ray single-crystal diffraction studies confirmed the formation of the BN and NBN motifs and the zigzag-edged topology of the regularly doped ribbons. Steady-state absorption and emission investigations at room temperature showed a systematic bathochromic shift of the UV–vis absorption and emission envelopes upon elongation of the oligoarylenyl backbone, with the nanoribbon emission featuring a TADF component. All derivatives displayed phosphorescence at 77 K. Electrochemical studies showed that the π-extension of the peri-acenoacene framework provokes a lowering of the first oxidative event (from 0.83 to 0.40 V), making these nanoribbons optimal candidates to engineer p-type organic semiconductors.
Matuszewska, O., Battisti, T., Ferreira, R.R., Biot, N., Demitri, N., Mézière, C., Allain, M., Sallé, M., Mañas-Valero, S., Coronado, E., Fresta, E., Costa, R..D. and Bonifazi, D. Chem. Eur. J. 2023, 29, e2022031. DOI: 10.1002/chem.202203115 Abstract Peri-thiaxanthenothiaxanthene, an S-doped analog of peri-xanthenoxanthene, is used as a polycyclic aromatic hydrocarbon (PAH) scaffold to tune the molecular semiconductor properties by editing the oxidation state of the S-atoms. Chemical oxidation of peri-thiaxanthenothiaxanthene with H2O2 led to the relevant sulfoxide and sulfone congeners, whereas electrooxidation gave access to sulfonium-type derivatives forming crystalline mixed valence (MV) complexes. These complexes depicted peculiar molecular and solid-state arrangements with face-to-face p-p stacking organization. Photophysical studies showed a widening of the optical bandgap upon progressive oxidation of the S-atoms, with the bis-sulfone derivative displaying the largest value (E00 = 2.99 eV). While peri-thiaxanthenothiaxanthene showed reversible oxidation properties, the sulfoxide and sulfone derivatives mainly showed reductive events, corroborating their n-type properties. Electric measurements of single crystals of the MV complexes exhibited a semiconducting behavior with a remarkably high conductivity at room temperature (10-1-10-2 S cm-1 and 10-2-10-3 S cm-1 for the O and S derivatives, respectively), one of the highest reported so far. Finally, the electroluminescence properties of the complexes were tested in light-emitting electrochemical cells (LECs), obtaining the first mid-emitting PAH-based LECs.
Sponsored by two of our on going EU projects, VIT and STiBNite, the summer school took place at the UniVie Skylounge conference room on 4-5 July 2022. We were delighted to host stimulating lectures both by external speakers and consortia representatives on the topic of self-assembled organic materials. Big thanks to our wonderful speakers Renaud Nicolay, Francesco Picchioni, Chiara Gualandi, Timothy Swager, Richard Kelly, Laura Maggini, Takuji Hatakeyama, Emilio Perez, Milan Kivala, Susana Otero, Alexander Kros! For more information about the STiBNite and VIT projects: https://stibnite.univie.ac.at/ and https://vit4europe.com/ These projects have received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie-Sklodowska-Curie grant agreements No 956923 and 101008237.