Design and synthesis of quadrupolar A-D-A photon absorbing molecules: An investigation into their optical and bioimaging properties

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-03-24 DOI:10.1016/j.dyepig.2025.112785

Shufan Yang , Konstantinos Bourdakos , Hiroki Cook , Anna Crisford , Ewan Forsyth , Sumeet Mahajan , Mark Bradley

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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.

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四极性A-D-A光子吸收分子的设计与合成：光学和生物成像特性的研究

本文报道了基于四极体受体-供体-受体体系的4种新型发色团的设计、合成及其光学性质。这些四极是用氟核设计的，偶联到噻吩基和噻吩基乙炔桥上，两个3-二氰维林丹-1- 1或两个1,3-双（二氰甲基）-吲哚作为强吸电子的部分。通过计算模型和光物理研究研究了结构-性质关系，荧光团发出具有大斯托克斯位移的红色发射。桥接的炔基单元，而不是增强共轭，显着降低了荧光强度和发射波长。值得注意的是，双光子吸收研究显示两个荧光团的横截面值δ = 1720和780 GM。利用单光子和双光子荧光生物成像技术，包括鸡骨的染色，探索了荧光团。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.