Triphenylamine/Tetracyanobutadiene-Based π-Conjugated Push-Pull Molecules End-Capped with Arene Platforms: Synthesis,...

π-Conjugated push-pull molecules based on triphenylamine and 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) have been functionalized with different terminal arene units. In solution, these highly TCBD-twisted systems showed a strong internal charge transfer band in the visible spectrum and no detectable photoluminescence (PL). Photophysical and theoretical investigations revealed very short singlet excited state deactivation time of ≈10 ps resulting from significant conformational changes of the TCBD-arene moiety upon photoexcitation, opening a pathway for non-radiative decay. The PL was recovered in vacuum-processed films or when the molecules were dispersed in a PMMA matrix leading to a significant increase of the excited state deactivation time. As shown by cyclic voltammetry, these molecules can act as electron donors compared to C₆₀ . Hence, vacuum-processed planar heterojunction organic solar cells were fabricated leading to a maximum power conversion efficiency of ca. 1.9 % which decreases with the increase of the arene size.