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Tripodal donor‐acceptor (D‐A) small molecules Tr‐Np3 and Tr‐T‐Np3 consisting of triphenyl triazine and 1,8‐naphthalimide, without and with a thiophene spacer have been synthesized. Their optical and redox properties were thoroughly investigated along with their utilization as photocatalysts in organic transformations. Compounds Tr‐Np3 and Tr‐T‐Np3 showed broad absorption in the range of 290–480 nm in solutions and 300–510 nm in thin films. These tripodal molecules displayed wide optical bandgaps of (Egopt) 3.10 eV and 2.64 eV with very deep‐lying HOMO energy levels (−6.60 eV and −6.03 eV) and low‐lying LUMO levels (−3.50 eV and −3.40 eV). Appreciable electron mobilities of 5.24×10−4 cm2/Vs and 6.14×10−4 cm2/Vs were obtained for compounds Tr‐Np3 and Tr‐T‐Np3 respectively by space‐charge limited current (SCLC) measurements. Metal‐free tripodal molecules Tr‐Np3 and Tr‐T‐Np3 showed excellent photocatalytic abilities towards condensation of aromatic aldehydes and o‐phenylenediamine followed by cyclization under visible light to yield benzimidazole derivatives that are of high medicinal value. [ABSTRACT FROM AUTHOR]