Palladium complexes of perylene diimides: Strong fluorescence despite direct attachment of late transition metals to organic dyes

Haim Weissman, Elijah Shirman, Tal Ben-Moshe, Revital Cohen, Gregory Leitus, Linda J W Shimon, Boris Rybtchinski

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

We prepared the first σ-bonded metal complexes of widely utilized organic dyes, perylene tetracarboxylic acid diimides (PDIs). These 1,7-dipalladium PDI complexes were synthesized by C-Br oxidative addition of 1,7-dibromo-N,N′-dicyclohexyl PDI (Br2PDI) to Pd(0) phosphine complexes bearing triphenylphosphine and bischelating 1,2-bis(diphenylphosphino) ethane (dppe). The structures of Pd-PDI complexes were elucidated by single-crystal X-ray analysis. Surprisingly, despite direct attachement of two late transition metal centers, Pd-PDI systems are highly fluorescent (Φ = 0.65 and 0.22 for triphenylphosphine and dppe systems, respectively). This is rationalized in terms of weak electronic interactions between the metal centers and PDI π-system, as revealed by TD-DFT calculations.

Original languageEnglish
Pages (from-to)4790-4792
Number of pages3
JournalInorganic Chemistry
Volume46
Issue number12
DOIs
Publication statusPublished - Jun 11 2007

Fingerprint

Perylene
Palladium
Transition metals
attachment
palladium
Coloring Agents
dyes
Fluorescence
transition metals
fluorescence
acids
Acids
phosphine
ethane
Bearings (structural)
Ethane
Coordination Complexes
X ray analysis
phosphines
Discrete Fourier transforms

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Palladium complexes of perylene diimides : Strong fluorescence despite direct attachment of late transition metals to organic dyes. / Weissman, Haim; Shirman, Elijah; Ben-Moshe, Tal; Cohen, Revital; Leitus, Gregory; Shimon, Linda J W; Rybtchinski, Boris.

In: Inorganic Chemistry, Vol. 46, No. 12, 11.06.2007, p. 4790-4792.

Research output: Contribution to journalArticle

Weissman, Haim ; Shirman, Elijah ; Ben-Moshe, Tal ; Cohen, Revital ; Leitus, Gregory ; Shimon, Linda J W ; Rybtchinski, Boris. / Palladium complexes of perylene diimides : Strong fluorescence despite direct attachment of late transition metals to organic dyes. In: Inorganic Chemistry. 2007 ; Vol. 46, No. 12. pp. 4790-4792.
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AU - Leitus, Gregory

AU - Shimon, Linda J W

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