Near-infrared emitting aza-BODIPY fluorophores, impact of N,N-dialkylamino groups on the photophysical properties: synthesis, characterization, and computational studies

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2025-08-01 Epub Date: 2025-03-22 DOI:10.1016/j.dyepig.2025.112773

Wassima Tajani , Ludmilla Verrieux , Annika Sickinger , Amélie Godard , Jean Rouillon , Christine Goze , Fabien Dalonneau , Yoann Rousselin , Olivier Maury , Lucie Sancey , Chantal Andraud , Boris Le Guennic , Arnaud Fihey , Ewen Bodio

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Abstract

The development of new fluorophores emitting in the near-infrared (NIR-I and/or NIR-II) region is currently a major focus of research in fields such as optics, energy, and medical imaging. Among these fluorophores, aza-BODIPYs have emerged as a particularly promising family. However, the challenge lies in determining which structural modifications are necessary to achieve the desired photophysical properties. This study aims to elucidate the impact of electron-donating groups, specifically N,N-dialkylamino groups, on these properties, depending on their number and position. A series of 14 aza-BODIPYs, without and with one to four N,N-dimethylamino groups, was synthesized, chemically characterized (NMR, HRMS, X-ray diffraction), and photochemically analyzed. Their photophysical properties were compared, and molecular modeling ((TD)-DFT) was performed to rationalize these properties. Preliminary tests in biological media were also conducted.

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近红外发射aza-BODIPY荧光团，N，N-二氨基对光物理性质的影响：合成，表征和计算研究

在近红外（NIR-I和/或NIR-II）区域发射的新荧光团的开发目前是光学，能源和医学成像等领域研究的主要焦点。在这些荧光团中，aza-BODIPYs已成为一个特别有前途的家族。然而，挑战在于确定哪些结构修改是必要的，以实现所需的光物理性质。本研究旨在阐明电子给基，特别是N，N-二烷基胺基，对这些性质的影响，取决于它们的数量和位置。合成了14个无或含1 - 4个N，N-二甲氨基基团的aza-BODIPYs，进行了化学表征（NMR， HRMS， x射线衍射），并进行了光化学分析。比较了它们的光物理性质，并用分子模型（(TD)-DFT）对这些性质进行了合理化分析。还在生物培养基中进行了初步试验。

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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.