Molecular design directs self-assembly of DPP polycatenars into 2D and 3D complex nanostructures

Novel diketopyrrolopyrrole (DPP) based polycatenars characterized with a long pi-conjugated rigid calamitic core, different side groups (t-Boc, H or PEO) at the lactam N atoms of the central DPP core and terminal hydrophobic paraffinic chains were prepared via Sonogashira coupling reaction as key steps. The influence of different side groups, different links and the length of terminal alkyl chains on the properties of these DPP derivatives was discussed. Such DPP polycaterners can self-assemble into bicontinuous cubic phase (Cub(v)/Ia3d) and hexagonal columnar phase (Col(hex)) in their pure states, as well as organogels in solution. UV and PL spectra investigation reveals that these compounds can display broad and strong absorption in the region of 275-650 nm and can emit in the NIR region (650-850 nm) with low energy gap (1.94 ev), meanwhile ICT effects have been detected between such DPP polycaternars and C-70, indicating the potential application of these compounds in solar cell. (C) 2022 Elsevier B.V. All rights reserved.

Automated summary

Novel DPP polycatenars with a long pi-conjugated rigid calamitic core, different side groups, and terminal hydrophobic chains were prepared via Sonogashira coupling reaction. These compounds can self-assemble into various phases and form organogels in solution. UV and fluorescence spectroscopy revealed their broad absorption and NIR emission, indicating their potential application in solar cells.