NDLI: Second-order nonlinear polarizability of ferrocene–BODIPY donor–acceptor adducts. Quantifying charge redistribution in the excited state

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Dalton Transactions Vol - 46 Issue - 3

Dalton Transactions Vol - 46 Issue - 2

Dalton Transactions Vol -39

Dalton Transactions Vol -0

Second-order nonlinear polarizability of ferrocene–BODIPY donor–acceptor adducts. Quantifying charge redistribution in the excited state

Content Provider	Royal Society of Chemistry (RSC)
Author	Singla, Priya Singh, Kamaljit Kaur, Navdeep Clays, Koen Steerteghem, Nick Van Kaur, Paramjit
Copyright Year	2017
Abstract	A series of dyads and triads using ferrocene (Fc) as the donor and 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) as the acceptor, linked either directly or through an N-phenylmethanimine or ethynylbenzene linker have been synthesized. While the former (directly linked) dyads were prepared through acid catalyzed condensation of pyrrole with ferrocenecarboxaldehye or 1,1′-ferrocenedicarboxaldehyde followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), the latter two sets (imine and alkyne linked) of dyads were obtained through Schiff base condensation or Sonogashira coupling reactions, respectively. The compounds were fully characterized with spectroscopic data and single crystal X-ray analysis in one case. The peaks corresponding to the Fe(II)/Fe(III) redox couple at 0.33 to 0.38 V showed a varying degree of positive anodic shift, which reflected the strong electron withdrawing effect of the corresponding BODIPY unit. The first hyperpolarisability, β, was measured in chloroform using the femtosecond hyper-Rayleigh scattering (HRS) method at 1300 nm. Interestingly, from the βHRS values, the dominating role of the Fc donor and the intervening linker could be established, which correlated well with the experimental linear optical data as well as theoretical data calculated using density functional theory (DFT) and time-dependent DFT calculations. This work constitutes the first report where electron accepting power of BODIPY in combination with the Fc donor moiety, is exploited and we demonstrate that the values are comparable to that of push–pull derivatives where BODIPY was used as the conjugated linker.
Starting Page	1124
Ending Page	1133
Page Count	10
File Format	HTM / HTML PDF
ISSN	14779226
Volume Number	46
Issue Number	4
Journal	Dalton Transactions
DOI	10.1039/c6dt04455g
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	BODIPY Schiff Ferrocene Carboxylic acid Pyrrole 3-Dichloro-5 6-dicyano-1 4-benzoquinone Imine Alkyne Schiff base Sonogashira coupling X-ray crystallography Redox Chloroform Femtosecond Sikorsky H-19 Chickasaw Nonlinear optics Density functional theory Push\u2013pull train
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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