p-Conjugated push-pull molecules based on triphenylamine and1 ,1,4,4-tetracyanobuta-1,3-diene (TCBD) have been functionalized with different terminal arene units. In solution, these highly TCBD-twisted systemss howeda 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 ap athway for non-radiative decay.T he PL was recovered in vacuum-processed films or when the moleculesw ere dispersed in aP MMA matrix leading to as ignificant increase of the excited state deactivation time. As shown by cyclic voltammetry,t hese molecules can act as electron donors compared to C 60 .H ence, vacuum-processedp lanar heterojunction organic solar cells were fabricated leading to am aximum power conversion efficiency of ca. 1.9 %w hich decreases with the increaseo ft he arene size.

The selective mono-nitration of benzothioxanthene (BTXI) is demonstrated here, opening doors to a wide range of structures and reactions. In addition, a new series of derivaties was characterized expanding the scope for electronic organic purposes.