Synthesis and characterisation of push-pull flavin dyes with efficient second harmonic generation (SHG) properties

Mohammed, N., Wiles, A. A. , Belsley, M., Fernandes, S. S.M., Cariello, M. , Rotello, V. M., Raposo, M. M. M. and Cooke, G. (2017) Synthesis and characterisation of push-pull flavin dyes with efficient second harmonic generation (SHG) properties. RSC Advances, 7(39), pp. 24462-24469. (doi: 10.1039/C7RA03400H)

Abstract

Organic compounds displaying second-order non-linear optical properties are key materials for optoelectronics. Here, three push–pull flavin derivates (FLA-A–C) have been synthesised and their optical, redox and second harmonic generation (SHG) properties have been investigated. In particular, we describe the role differing electron donor units (N,N-dimethylaniline-, N,N-diphenylaniline- and ferrocenyl-) attached through the C(8) position of the flavin unit have on the optical and redox properties of the latter. Hyper-Rayleigh scattering in dioxane solutions using a fundamental wavelength of 1064 nm was employed to evaluate their second-order nonlinear optical properties. Our experiments have indicated that their first hyperpolarisabilities (β) are influenced by the electronic nature and strength of the donor groups. N,N-dimethylaniline-functionalised derivative FLA-A, exhibited the largest first hyperpolarisability (β = 9550 × 10−30 esu, using the T convention) and high decomposition temperature (Td = 312 °C), thus indicating its potential application as a useful material for incorporation into non-linear optical devices.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Cariello, Dr Michele and Cooke, Professor Graeme and Mohammed, Nabeel and Wiles, Dr Alan
• Authors: Mohammed, N., Wiles, A. A., Belsley, M., Fernandes, S. S.M., Cariello, M., Rotello, V. M., Raposo, M. M. M., and Cooke, G.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: RSC Advances
• Publisher: Royal Society of Chemistry
• ISSN: 2046-2069
• ISSN (Online): RSC Advances
• Copyright Holders: Copyright © 2017 The Authors
• First Published: First published in RSC Advances 7(39):24462-24469
• Publisher Policy: Reproduced under a Creative Commons License

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
44504	1	Physical organic chemistry - opportunities in synthesis, materials and pharmaceuticals	Graeme Cooke	Engineering & Physical Sciences Research Council (EPSRC)	EP/E036244/1	CHEM - CHEMISTRY