@article{ravikanth_strachan_li_lindsey_1998, title={Trans-substituted porphyrin building blocks bearing iodo and ethynyl groups for applications in bioorganic and materials chemistry}, volume={54}, ISSN={["0040-4020"]}, DOI={10.1016/S0040-4020(98)00408-6}, abstractNote={The modular synthesis of linear or cyclic multiporphyrin arrays relies on the availability of trans-substituted porphyrin building blocks with high solubility in organic solvents. Eleven porphyrin building blocks were synthesized bearing iodo, ethynyl, and 2-(trimethylsilyl)ethynyl groups at the 4-, 3-, or 3,5-positions of two meso-aryl units, and mesityl groups at the other two meso-positions. The synthesis involves condensation of 5-mesityldipyrromethane with one or two aryl aldehydes. Combinations of functional groups include di-iodo, tetra-iodo, bis[(2-(trimethylsilyl)ethynyl], iodo and 2-(trimethylsilyl)ethynyl, and ethynyl and 2-(trimethylsilyl)ethynyl. In addition, a porphyrin bearing one 4-iodophenyl group and one 3,5-bis(boron-dipyrrin)phenyl group was synthesized for applications in molecular photonic devices. The iodo and ethynyl groups are ideally-suited for Pd-mediated coupling reactions, allowing the porphyrin building blocks to be joined in the systematic construction of soluble multiporphyrin arrays.}, number={27}, journal={TETRAHEDRON}, author={Ravikanth, M and Strachan, JP and Li, FR and Lindsey, JS}, year={1998}, month={Jul}, pages={7721–7734} }