Design and synthesis of quadrupolar A-D-A photon absorbing molecules: an investigation into their optical and bioimaging properties
Design and synthesis of quadrupolar A-D-A photon absorbing molecules: an investigation into their optical and bioimaging properties
We herein report on the design and synthesis and optical properties of 4 novel chromophores based on a quadrupole acceptor-donor-acceptor system. These quadrupoles were designed using a fluorene core, coupled to thienyl and thienyl acetylene bridges, to either two 3-dicycanovinylindan-1-ones or two 1,3-bis(dicyanomethylidene)-indanes as strong electron-withdrawing moieties. The structure-property relationships were investigated by computational modelling and photophysical studies, with the fluorophores giving red-emission with large Stokes shifts. The bridged alkynyl units, rather than enhancing conjugation, dramatically reduced fluorescence intensities and wavelength of emission. Notably, two-photon absorption studies revealed cross-section values of δ = 1720 and 780 GM for two of the fluorophores. The fluorophores were explored in one-photon and two-photon fluorescence biological imaging, including the staining of chick bones.
Yang, Shufan
29598279-7d3f-415a-a42c-054c87b47d7d
Bourdakos, Konstantinos
83f6fc3a-db12-476b-9a78-4aad8756f82f
Cook, Hiroki
52913239-643d-4ca5-bc0b-9479e133d53b
Crisford, Anna
135675e1-a172-4d93-989b-93d1efb022c3
Forsyth, Ewan
e4836e26-bad0-4500-8445-255ce85195c4
Mahajan, Sumeet
3e8fb3d0-f384-4182-ac26-b3063056a3c6
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900
29 March 2025
Yang, Shufan
29598279-7d3f-415a-a42c-054c87b47d7d
Bourdakos, Konstantinos
83f6fc3a-db12-476b-9a78-4aad8756f82f
Cook, Hiroki
52913239-643d-4ca5-bc0b-9479e133d53b
Crisford, Anna
135675e1-a172-4d93-989b-93d1efb022c3
Forsyth, Ewan
e4836e26-bad0-4500-8445-255ce85195c4
Mahajan, Sumeet
3e8fb3d0-f384-4182-ac26-b3063056a3c6
Bradley, Mark
562b9add-34c4-4620-bfa1-c7c83a0f0900
Yang, Shufan, Bourdakos, Konstantinos, Cook, Hiroki, Crisford, Anna, Forsyth, Ewan, Mahajan, Sumeet and Bradley, Mark
(2025)
Design and synthesis of quadrupolar A-D-A photon absorbing molecules: an investigation into their optical and bioimaging properties.
Dyes and Pigments, 239, [112785].
(doi:10.1016/j.dyepig.2025.112785).
Abstract
We herein report on the design and synthesis and optical properties of 4 novel chromophores based on a quadrupole acceptor-donor-acceptor system. These quadrupoles were designed using a fluorene core, coupled to thienyl and thienyl acetylene bridges, to either two 3-dicycanovinylindan-1-ones or two 1,3-bis(dicyanomethylidene)-indanes as strong electron-withdrawing moieties. The structure-property relationships were investigated by computational modelling and photophysical studies, with the fluorophores giving red-emission with large Stokes shifts. The bridged alkynyl units, rather than enhancing conjugation, dramatically reduced fluorescence intensities and wavelength of emission. Notably, two-photon absorption studies revealed cross-section values of δ = 1720 and 780 GM for two of the fluorophores. The fluorophores were explored in one-photon and two-photon fluorescence biological imaging, including the staining of chick bones.
Text
1-s2.0-S014372082500155X-main
- Version of Record
More information
Accepted/In Press date: 24 March 2025
e-pub ahead of print date: 24 March 2025
Published date: 29 March 2025
Identifiers
Local EPrints ID: 500934
URI: http://eprints.soton.ac.uk/id/eprint/500934
ISSN: 0143-7208
PURE UUID: 5e22a5e1-2532-4cc1-85b5-ee6891a824a2
Catalogue record
Date deposited: 19 May 2025 16:46
Last modified: 22 Aug 2025 02:47
Export record
Altmetrics
Contributors
Author:
Shufan Yang
Author:
Konstantinos Bourdakos
Author:
Hiroki Cook
Author:
Ewan Forsyth
Author:
Sumeet Mahajan
Author:
Mark Bradley
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics