Orange-red emissive coumarin based quadrupolar dyes: Synthesis, photophysical and DFT studies

IF 4.1 3区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Photochemistry and Photobiology A-chemistry Pub Date : 2024-09-19 DOI:10.1016/j.jphotochem.2024.116045

Puja O. Gupta , Nagaiyan Sekar

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Abstract

Designing and synthesized dyes with diethylamino coumarin as fixed and diethylamino coumarin, julolidine, and pyrene-based donors with dicynovinylene acceptor, the effects of donor and π-linker on linear and non-linear optical (NLO) properties were examined. Density functional theory (DFT) and time-dependent DFT were used for this investigation. Maximum absorption and emission were seen in the range of 500–547, 525–569, and 420–429 nm, as well as 576–653, 592–653, and 492–536 nm for diethylamino coumarin, julolidine, and pyrene-based dyes. A julolidine-based donor dye showed red-shifted absorption and emission properties compared to diethylamino and pyrene-based coumarin. All dyes in polar demonstrated significant viscosity sensitivity (PEG: methanol) solutions. Furthermore, above 250°C, the title dyes demonstrated good thermal stability. Additionally, the theoretical analysis suggested that dyes based on julolidine have superior linear and NLO properties in solvent phases and better CT (as determined by FMO, MEP, BLA, and BOA calculations).

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基于香豆素的橙红色发射型四极染料：合成、光物理和 DFT 研究

设计并合成了以二乙胺基香豆素为固定体，以二乙胺基香豆素、茱莉定和芘为供体，以二炔乙烯为受体的染料，研究了供体和π-连接剂对线性和非线性光学（NLO）特性的影响。研究采用了密度泛函理论（DFT）和随时间变化的 DFT。二乙氨基香豆素、久洛立定和芘基染料在 500-547、525-569 和 420-429 nm 以及 576-653、592-653 和 492-536 nm 波长范围内具有最大吸收和发射。与二乙基氨基香豆素和芘基香豆素相比，鸦胆子苷基供体染料显示出红移吸收和发射特性。所有染料在极性（PEG：甲醇）溶液中都表现出明显的粘度敏感性。此外，在 250°C 以上，标题染料表现出良好的热稳定性。此外，理论分析表明，基于久洛尼定的染料在溶剂相中具有优异的线性和 NLO 特性，以及更好的 CT（由 FMO、MEP、BLA 和 BOA 计算确定）。

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来源期刊

Journal of Photochemistry and Photobiology A-chemistry 化学-物理化学

CiteScore

7.90

自引率

7.00%

发文量

580

审稿时长

48 days

期刊介绍： JPPA publishes the results of fundamental studies on all aspects of chemical phenomena induced by interactions between light and molecules/matter of all kinds. All systems capable of being described at the molecular or integrated multimolecular level are appropriate for the journal. This includes all molecular chemical species as well as biomolecular, supramolecular, polymer and other macromolecular systems, as well as solid state photochemistry. In addition, the journal publishes studies of semiconductor and other photoactive organic and inorganic materials, photocatalysis (organic, inorganic, supramolecular and superconductor). The scope includes condensed and gas phase photochemistry, as well as synchrotron radiation chemistry. A broad range of processes and techniques in photochemistry are covered such as light induced energy, electron and proton transfer; nonlinear photochemical behavior; mechanistic investigation of photochemical reactions and identification of the products of photochemical reactions; quantum yield determinations and measurements of rate constants for primary and secondary photochemical processes; steady-state and time-resolved emission, ultrafast spectroscopic methods, single molecule spectroscopy, time resolved X-ray diffraction, luminescence microscopy, and scattering spectroscopy applied to photochemistry. Papers in emerging and applied areas such as luminescent sensors, electroluminescence, solar energy conversion, atmospheric photochemistry, environmental remediation, and related photocatalytic chemistry are also welcome.