Near-infrared absorbing hydrogen-bonded dithioketopyrrolopyrrole (DTPP) n-type semiconductors

0555817 - FZÚ 2023 RIV GB eng J - Journal Article
Kratochvíl, M. - Cigánek, M. - Yumusak, C. - Seelajaroen, H. - Císařová, I. - Fábry, Jan - Vala, M. - Luňák, S. - Weiter, M. - Sariciftci, N. S. - Krajčovič, J.
Near-infrared absorbing hydrogen-bonded dithioketopyrrolopyrrole (DTPP) n-type semiconductors.
Dyes and Pigments. Roč. 197, Jan (2022), č. článku 109884. ISSN 0143-7208. E-ISSN 1873-3743
Research Infrastructure: CESNET II - 90042
Institutional support: RVO:68378271
Keywords : organic photovoltaics * hydrogen-bonded pigments * dithioketopyrrolopyrrole * diketopyrrolopyrrole * n-type semiconductors
OECD category: Physical chemistry
Impact factor: 4.5, year: 2022
Method of publishing: Limited access
https://doi.org/10.1016/j.dyepig.2021.109884

Well-known 1,4-diketo-3,6-diphenyl-pyrrolo-[3,4-c]-pyrrole (Ph-DPP) and 1,4-diketo-3,6-(thiophen-2-yl)-pyrrolo-[3,4-c]-pyrrole (Th-DPP) were transformed to their 1,4-dithioketo heteroanalogues (Ph-DTPP and Th-DTPP). X-ray single crystal structure determination confirmed the presence of CS-HN hydrogen bonds and a similar stack formation in both DTPPs, leading to relatively high decomposition temperatures, about 350 ◦C. According to density functional theory (DFT) calculations, thionation left HOMO (π-type) level almost unchanged, considerably destabilized non-bonding orbital (n-orbital) localized on thioketo group, and significantly decreased LUMO (π*-type) energy. Evolution of HOMO and LUMO energies was confirmed by cyclic voltammetry, establishing LUMO energy at 4.5 eV for both DTPPs.
Permanent Link: http://hdl.handle.net/11104/0330269