Energy
transfer plays a special role in photocatalysis by utilizing
the potential energy of the excited state through indirect excitation,
in which a photosensitizer determines the thermodynamic feasibility
of the reaction. Bioinspired by the energy-transfer ability of natural
product cercosporin, here we developed a green and highly efficient
organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin)
through structural modification of cercosporin. After structural manipulation,
its triplet energy was greatly improved, and then, it could markedly
promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it
was also effective for energy-transfer-mediated organometallic catalysis,
which allowed realization of the cross-coupling of aryl bromides and
carboxylic acids through efficient energy transfer from HiBRCP to
nickel complexes. Thus, the study on the relationship between structural
manipulation and their photophysical properties provided guidance
for further modification of cercosporin, which could be applied to
more meaningful and challenging energy-transfer reactions.