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Decaphyrin Conformers Stabilized by Pseudo-Rigid Dipyrrolylbenzothiadiazole Blocks: Synthesis, Structures and
Zhen Yang1, Glib Baryshnikov2, Shijun Li3
1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Shanghai Key Laboratory of Functional Materials Chemistry, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, 200237, China.
None:
Two conformers of a dipyrrolylbenzothiadiazole (DP-BTD) embedded decaphyrin(1.1.1.0.0.1.1.1.0.0) have been synthesized and separated, exhibiting crescent-shaped and figure-eight conformations, respectively. Incorporation of the hydrogen bonding-reinforced pseudorigid and electron-withdrawing DP-BTD segments not only stabilizes the distinct conformations, but also extends the absorption to ca. 1600 nm due to the good conjugation and ICT effect. Although both conformers are stable at room temperature, reversible interconversion occurs between them upon heating or disrupting intramolecular hydrogen bonds by protonation.
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