Supramolecular triplet photosensitizers based on hydrogen bonding-mediated molecular assemblies were prepared. Three thymine-containing visible light-harvesting Bodipy derivatives (B-1, B-2 and B-3, which show absorption at 505 nm, 630 nm and 593 nm, respectively), were used as one of the H-bonding module, and 1,6-diaminopyridine appended C60 was used as the complementary hydrogen bonding module (C-1), in which the C60 part is as the spin converter to produce triplet state. Visible light-harvesting antenna with methylated thymine were prepared as references (B-1-Me, B-2-Me and B-3-Me), which are unable to form strong H-bond with C-1. Triple H-bonds are formed between each Bodipy antenna (B-1, B-2 and B-3) and the C60 module (C-1). The photophysical propertied of the H-bond assemblies and the reference non-hydrogen bond-forming mixtures were studied with steady state UV/vis absorption spectroscopy, fluorescence emission spectroscopy, electrochemical data, and nanosecond transient absorption spectroscopies. Singlet energy transfer from the Bodipy antenna to the C60 module was confirmed by fluorescence quenching studies. The intersystem crossing of the latter produce the triplet excited state. The nanosecond transient absorption spectroscopy shows that the triplet state is either localized on the C60 module (assembly B-1•C-1), or on the styrylBodipy antenna (for assemblies B-2•C-1 and B-3•C-1). Intraassembly ping-pong singlet/transfer energy transfer were proposed. In contrast to the H-bonding assemblies, slow triplet energy transfer was observed for the non-hydrogen bonding mixtures. These supramolecular assemblies were used as triplet photosensitizers for triplet-triplet annihilation upconversion.