Molecular Self-recovery Features of Naphthyl Derivatives of Pyrimidine Bis Hydrazones: AIE, Mechanochromism and Al3+/Pyrophosphate (PPi) sensing

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-09-02 DOI:10.1016/j.dyepig.2025.113186

Ottoor Anitha , Janardhanan Aiswarya , Rajendran Kishore Kumar , Sandipan Ghorai , Thangaraj Thiruppathiraja , Ramalingam Natarajan , Senthilkumar Lakshmipathi , Balasubramanian Murugesapandian

{"title":"Molecular Self-recovery Features of Naphthyl Derivatives of Pyrimidine Bis Hydrazones: AIE, Mechanochromism and Al3+/Pyrophosphate (PPi) sensing","authors":"Ottoor Anitha , Janardhanan Aiswarya , Rajendran Kishore Kumar , Sandipan Ghorai , Thangaraj Thiruppathiraja , Ramalingam Natarajan , Senthilkumar Lakshmipathi , Balasubramanian Murugesapandian","doi":"10.1016/j.dyepig.2025.113186","DOIUrl":null,"url":null,"abstract":"<div><div>In this study, we have formulated and synthesized two compounds, HPHNP and HPOMNP, by engaging in chemical reactions that involve pyrimidine bishydrazides with 2-hydroxy-1-naphthaldehyde and 2-methoxy-1-naphthaldehyde, respectively. The compound HPHNP displays partial excited-state intramolecular proton transfer (ESIPT) characteristics in non-polar aprotic solvents due to a phenolic group. Both HPHNP and HPOMNP exhibit aggregation-induced emission (AIE) behavior in DMF-water mixtures, with varying water fractions. We investigated how HPHNP and HPOMNP behave when exposed to mechanical pressure and found a remarkable effect called molecular motion or self-recovery. Solid-state emission experiments, PXRD measurements, and theoretical analyses support this observation. Moreover, HPHNP serves as an efficient fluorescent probe for detecting Al3+ and pyrophosphate (PPi) ions in a DMF-water mixture with an 80% water fraction. The potential for solid-state motion is expected to have a crucial role in advancing molecular machines, and we anticipate that our findings will inspire other researchers by highlighting the utilization of intermolecular forces to achieve solid-state motion.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"245 ","pages":"Article 113186"},"PeriodicalIF":4.2000,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S014372082500556X","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

Abstract

In this study, we have formulated and synthesized two compounds, HPHNP and HPOMNP, by engaging in chemical reactions that involve pyrimidine bishydrazides with 2-hydroxy-1-naphthaldehyde and 2-methoxy-1-naphthaldehyde, respectively. The compound HPHNP displays partial excited-state intramolecular proton transfer (ESIPT) characteristics in non-polar aprotic solvents due to a phenolic group. Both HPHNP and HPOMNP exhibit aggregation-induced emission (AIE) behavior in DMF-water mixtures, with varying water fractions. We investigated how HPHNP and HPOMNP behave when exposed to mechanical pressure and found a remarkable effect called molecular motion or self-recovery. Solid-state emission experiments, PXRD measurements, and theoretical analyses support this observation. Moreover, HPHNP serves as an efficient fluorescent probe for detecting Al³⁺ and pyrophosphate (PPi) ions in a DMF-water mixture with an 80% water fraction. The potential for solid-state motion is expected to have a crucial role in advancing molecular machines, and we anticipate that our findings will inspire other researchers by highlighting the utilization of intermolecular forces to achieve solid-state motion.

Abstract Image

查看原文本刊更多论文

嘧啶双腙萘基衍生物的分子自恢复特性：AIE、机械致色性和Al3+/焦磷酸（PPi）传感

在本研究中，我们通过嘧啶双酰肼与2-羟基-1-萘醛和2-甲氧基-1-萘醛的化学反应，分别配制并合成了HPHNP和HPOMNP两个化合物。化合物HPHNP在非极性非质子溶剂中表现出部分激发态分子内质子转移（ESIPT）特性。HPHNP和HPOMNP在dmf -水混合物中表现出聚集诱导发射（AIE）行为，具有不同的水组分。我们研究了HPHNP和HPOMNP在暴露于机械压力下的表现，并发现了一种称为分子运动或自我恢复的显着效应。固体发射实验、PXRD测量和理论分析都支持这一观察结果。此外，HPHNP可以作为一种高效的荧光探针，用于检测80%水分数的dmf -水混合物中的Al3+和焦磷酸盐（PPi）离子。固态运动的潜力有望在推进分子机器方面发挥关键作用，我们预计我们的发现将通过强调利用分子间力来实现固态运动来激励其他研究人员。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.