Tuning the reactivity of dioxoruthenium(VI) porphyrins toward an arylimine by altering porphyrin substituents |
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| Authors: | Huang Jie-Sheng Leung Sarana Ka-Yan Zhou Zhong-Yuan Zhu Nianyong Che Chi-Ming |
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| Institution: | Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong. jshuang@hku.hk |
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| Abstract: | Reaction of dioxoruthenium(VI) porphyrins Ru(VI)(Por)O2] with arylimine HN=CPh2 in dichloromethane afforded bis(methyleneamido)ruthenium(IV) porphyrins Ru(IV)(Por)(N=CPh2)2] for Por = 4-Cl-TPP and TMP; (methyleneamido)hydroxoruthenium(IV) porphyrins Ru(IV)(Por)(N=CPh2)(OH)] for Por = TPP and TTP; and bis(arylimine)ruthenium(II) porphyrins Ru(II)(Por)(HN=CPh2)2] for Por = 3,5-Cl2TPP and 3,5-(CF3)2TPP. In dichloromethane solution exposed to air, complex Ru(II)(3,5-Cl2TPP)(HN=CPh2)2] underwent oxidative deprotonation to form Ru(IV)(3,5-Cl2TPP)(N=CPh2)2]. The new ruthenium porphyrins were identified by 1H NMR, UV-vis, IR, and mass spectroscopy, along with elemental analysis. X-ray crystal structure determinations of Ru(IV)(4-Cl-TPP)(N=CPh2)2], Ru(IV)(TPP)(N=CPh2)(OH)], and Ru(II)(3,5-(CF3)2TPP)(HN=CPh2)2] revealed the Ru-N(methyleneamido) or Ru-N(arylimine) distances of 1.897(5) A (average), 1.808(4) A, and 2.044(2) A (average), respectively. |
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