Tricyanofuran (TCF) derivatives attached to both anthracene and pyrene moieties were synthesised and characterised by optical, electrochemical and computational techniques. Both compounds exhibited similar absorption profile as well as electrochemical behaviour, however the pyrene derivative showed 20-fold higher non-linear optical activity measured by the EFISH technique. This huge difference has been assigned to (i) a lower molar absorption and (ii) a higher torsion angle for the anthracene derivative, confirmed by both experimental X-ray diffraction and DFT calculations. Furthermore, we note that the μβ1.907 value of -1700 × 10(-48) esu recorded for the pyrene derivative in CHCl3/pyridine is remarkable for a NLO chromophore lacking a classical push-pull structure.

Effect of torsional twist on 2nd order non-linear optical activity of anthracene and pyrene tricyanofuran derivatives / M. Planells, M. Pizzotti, G.S. Nichol, F. Tessore, N. Robertson. - In: PHYSICAL CHEMISTRY CHEMICAL PHYSICS. - ISSN 1463-9084. - 16:42(2014 Nov 14), pp. 23404-23411. [10.1039/c4cp03509g]

Effect of torsional twist on 2nd order non-linear optical activity of anthracene and pyrene tricyanofuran derivatives

M. Pizzotti
Secondo
;
F. Tessore
Penultimo
;
2014

Abstract

Tricyanofuran (TCF) derivatives attached to both anthracene and pyrene moieties were synthesised and characterised by optical, electrochemical and computational techniques. Both compounds exhibited similar absorption profile as well as electrochemical behaviour, however the pyrene derivative showed 20-fold higher non-linear optical activity measured by the EFISH technique. This huge difference has been assigned to (i) a lower molar absorption and (ii) a higher torsion angle for the anthracene derivative, confirmed by both experimental X-ray diffraction and DFT calculations. Furthermore, we note that the μβ1.907 value of -1700 × 10(-48) esu recorded for the pyrene derivative in CHCl3/pyridine is remarkable for a NLO chromophore lacking a classical push-pull structure.
electronic-properties; chromophores; donor; acceptor; hyperpolarizabilities; molecules; polyenes; state; coordination; aggregation
Settore CHIM/03 - Chimica Generale e Inorganica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/249645
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