Chiral ruthenium-terpyridine based metallodendrimers: Facile synthesis, characterization, and photophysical studies

Hua Jiang, Suk Joong Lee, Wenbin Lin

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Abstract

The new chiral ligand 4′-[6-(2,2′-diethoxy-1,1′-binaphthyl)]-2,2′: 6′,2″-terpyridine (L1) was synthesized in three steps in 47% overall yield starting from 6,6′-dibromo-2,2′-diethoxy-1,1′-binaphthalene. L1 was quantitatively converted to 4′-[6-(2,2′-dihydroxy-1,1′-binaphthyl)]-2,2′: 6′,2″-terpyridine (L2) by treatment with BBr3, while L2 was treated with tert-butyldimethylsilyl chloride to give to 4′-{6-[2,2′-bis(tert-butyldimethylsiloxy)-1,1′- binaphthyl]}-2,2′:6′,2″-terpyridine (L3) in high yields. These new chiral terpyridine ligands L1-3 were coordinated to Ru(III) centers to generate Ru(L1-3)Cl3 which were then treated with the tetrakis(terpyridine) core in the presence of 4-ethylmorpholine to afford chiral Ru(terpy)2 2+ based metallodendrimers containing enantiopure 1,1′-bi-2-naphthyl units in their peripheries. These chiral metallodendrimers were characterized by NMR, ESI-MS, and cyclic voltammetry, while their photophysical properties were studied using UV-Vis, luminescence, and circular dichroism spectroscopies.

Original languageEnglish
Pages (from-to)3429-3433
Number of pages5
JournalJournal of the Chemical Society, Dalton Transactions
Issue number18
Publication statusPublished - 2002 Nov 6
Externally publishedYes

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Ruthenium
Circular dichroism spectroscopy
Ligands
Cyclic voltammetry
Luminescence
Nuclear magnetic resonance
N-ethylmorpholine
tert-butyldimethylsilyl chloride

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Chiral ruthenium-terpyridine based metallodendrimers: Facile synthesis, characterization, and photophysical studies",
abstract = "The new chiral ligand 4′-[6-(2,2′-diethoxy-1,1′-binaphthyl)]-2,2′: 6′,2″-terpyridine (L1) was synthesized in three steps in 47{\%} overall yield starting from 6,6′-dibromo-2,2′-diethoxy-1,1′-binaphthalene. L1 was quantitatively converted to 4′-[6-(2,2′-dihydroxy-1,1′-binaphthyl)]-2,2′: 6′,2″-terpyridine (L2) by treatment with BBr3, while L2 was treated with tert-butyldimethylsilyl chloride to give to 4′-{6-[2,2′-bis(tert-butyldimethylsiloxy)-1,1′- binaphthyl]}-2,2′:6′,2″-terpyridine (L3) in high yields. These new chiral terpyridine ligands L1-3 were coordinated to Ru(III) centers to generate Ru(L1-3)Cl3 which were then treated with the tetrakis(terpyridine) core in the presence of 4-ethylmorpholine to afford chiral Ru(terpy)2 2+ based metallodendrimers containing enantiopure 1,1′-bi-2-naphthyl units in their peripheries. These chiral metallodendrimers were characterized by NMR, ESI-MS, and cyclic voltammetry, while their photophysical properties were studied using UV-Vis, luminescence, and circular dichroism spectroscopies.",
author = "Hua Jiang and Lee, {Suk Joong} and Wenbin Lin",
year = "2002",
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N2 - The new chiral ligand 4′-[6-(2,2′-diethoxy-1,1′-binaphthyl)]-2,2′: 6′,2″-terpyridine (L1) was synthesized in three steps in 47% overall yield starting from 6,6′-dibromo-2,2′-diethoxy-1,1′-binaphthalene. L1 was quantitatively converted to 4′-[6-(2,2′-dihydroxy-1,1′-binaphthyl)]-2,2′: 6′,2″-terpyridine (L2) by treatment with BBr3, while L2 was treated with tert-butyldimethylsilyl chloride to give to 4′-{6-[2,2′-bis(tert-butyldimethylsiloxy)-1,1′- binaphthyl]}-2,2′:6′,2″-terpyridine (L3) in high yields. These new chiral terpyridine ligands L1-3 were coordinated to Ru(III) centers to generate Ru(L1-3)Cl3 which were then treated with the tetrakis(terpyridine) core in the presence of 4-ethylmorpholine to afford chiral Ru(terpy)2 2+ based metallodendrimers containing enantiopure 1,1′-bi-2-naphthyl units in their peripheries. These chiral metallodendrimers were characterized by NMR, ESI-MS, and cyclic voltammetry, while their photophysical properties were studied using UV-Vis, luminescence, and circular dichroism spectroscopies.

AB - The new chiral ligand 4′-[6-(2,2′-diethoxy-1,1′-binaphthyl)]-2,2′: 6′,2″-terpyridine (L1) was synthesized in three steps in 47% overall yield starting from 6,6′-dibromo-2,2′-diethoxy-1,1′-binaphthalene. L1 was quantitatively converted to 4′-[6-(2,2′-dihydroxy-1,1′-binaphthyl)]-2,2′: 6′,2″-terpyridine (L2) by treatment with BBr3, while L2 was treated with tert-butyldimethylsilyl chloride to give to 4′-{6-[2,2′-bis(tert-butyldimethylsiloxy)-1,1′- binaphthyl]}-2,2′:6′,2″-terpyridine (L3) in high yields. These new chiral terpyridine ligands L1-3 were coordinated to Ru(III) centers to generate Ru(L1-3)Cl3 which were then treated with the tetrakis(terpyridine) core in the presence of 4-ethylmorpholine to afford chiral Ru(terpy)2 2+ based metallodendrimers containing enantiopure 1,1′-bi-2-naphthyl units in their peripheries. These chiral metallodendrimers were characterized by NMR, ESI-MS, and cyclic voltammetry, while their photophysical properties were studied using UV-Vis, luminescence, and circular dichroism spectroscopies.

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