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 language | English |
|---|---|
| Pages (from-to) | 4790-4792 |
| Number of pages | 3 |
| Journal | Inorganic Chemistry |
| Volume | 46 |
| Issue number | 12 |
| DOIs | |
| Publication status | Published - Jun 11 2007 |
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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 journal › Article
}
TY - JOUR
T1 - Palladium complexes of perylene diimides
T2 - Strong fluorescence despite direct attachment of late transition metals to organic dyes
AU - Weissman, Haim
AU - Shirman, Elijah
AU - Ben-Moshe, Tal
AU - Cohen, Revital
AU - Leitus, Gregory
AU - Shimon, Linda J W
AU - Rybtchinski, Boris
PY - 2007/6/11
Y1 - 2007/6/11
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=34347249193&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34347249193&partnerID=8YFLogxK
U2 - 10.1021/ic700539b
DO - 10.1021/ic700539b
M3 - Article
C2 - 17503813
AN - SCOPUS:34347249193
VL - 46
SP - 4790
EP - 4792
JO - Inorganic Chemistry
JF - Inorganic Chemistry
SN - 0020-1669
IS - 12
ER -