Aditi Garg, Umesh R. Pratap, Abhishek Banerjee* and Sujit Kumar Ghosh*,
{"title":"开发基于萘二甲酰亚胺的双态发射有机探针:从固态到溶液相的有趣协同效应","authors":"Aditi Garg, Umesh R. Pratap, Abhishek Banerjee* and Sujit Kumar Ghosh*, ","doi":"10.1021/acs.cgd.4c0086710.1021/acs.cgd.4c00867","DOIUrl":null,"url":null,"abstract":"<p >Luminescent compounds have garnered significant interest for their wide range of applications in light harvesting, cell imagining, LASERs, light-emitting diodes, etc. Conventional luminescent organic molecules show their emissive properties in the solution phase; however, in the solid state, a quenching of the fluorescence intensity occurs. Researchers have been able to overcome such challenges using the phenomenon of aggregation-induced emission (AIE), which enhances the solid-state emissive properties through close packing aided by nonbonded interactions. Such molecules, conventionally referred to as AIE luminogens, are observed to show phase-exclusive emissive properties, i.e., emissive in the solid state but nonemissive in the solution phase. Such drawbacks have prompted us to investigate molecules having emissive properties in both solution and solid phase, viz., dual-state emissive molecules [dual-state emission (DSE) luminogens]. Among these, naphthalimides, owing to their versatile conformational arrangements, are of prime interest. In this article, we present the design, synthesis, structural characterization, and detailed spectroscopic studies of a naphthalimide-based luminogen molecule, 6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-(6-methoxybenzothiazol-2-yl)-1<i>H</i>-benzoisoquinoline-1,3(2<i>H</i>)-dione (<b>HPMTB</b>). Single-crystal X-ray diffraction studies in the solid state have provided detailed structural information as well as the molecular packing arrangement of the molecule <b>HPMTB</b> along three dimensions. Solution-phase and solid-state fluorescence studies have revealed the existence of aggregation-induced emissive and mechanofluorochromic properties within the molecule. Detailed solution-phase photophysical investigations of <b>HPMTB</b> have revealed the existence of aggregates in a protic polar solvent (water) via the accumulation of flakes. Solid-state emission also shows the existence of reversible mechanofluorochromism in <b>HPMTB</b>. The current work develops materials that can attain DSE and mechanofluorochromism and sets up the foundation for the development of naphthalimide-based organic molecules for use as luminescent smart materials.</p>","PeriodicalId":34,"journal":{"name":"Crystal Growth & Design","volume":"24 18","pages":"7632–7643 7632–7643"},"PeriodicalIF":3.2000,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Development of a Dual-State Emissive Naphthalimide-Based Organic Probe: Interesting Synergistic Effects from the Solid State to the Solution Phase\",\"authors\":\"Aditi Garg, Umesh R. Pratap, Abhishek Banerjee* and Sujit Kumar Ghosh*, \",\"doi\":\"10.1021/acs.cgd.4c0086710.1021/acs.cgd.4c00867\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Luminescent compounds have garnered significant interest for their wide range of applications in light harvesting, cell imagining, LASERs, light-emitting diodes, etc. Conventional luminescent organic molecules show their emissive properties in the solution phase; however, in the solid state, a quenching of the fluorescence intensity occurs. Researchers have been able to overcome such challenges using the phenomenon of aggregation-induced emission (AIE), which enhances the solid-state emissive properties through close packing aided by nonbonded interactions. Such molecules, conventionally referred to as AIE luminogens, are observed to show phase-exclusive emissive properties, i.e., emissive in the solid state but nonemissive in the solution phase. Such drawbacks have prompted us to investigate molecules having emissive properties in both solution and solid phase, viz., dual-state emissive molecules [dual-state emission (DSE) luminogens]. Among these, naphthalimides, owing to their versatile conformational arrangements, are of prime interest. In this article, we present the design, synthesis, structural characterization, and detailed spectroscopic studies of a naphthalimide-based luminogen molecule, 6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-(6-methoxybenzothiazol-2-yl)-1<i>H</i>-benzoisoquinoline-1,3(2<i>H</i>)-dione (<b>HPMTB</b>). Single-crystal X-ray diffraction studies in the solid state have provided detailed structural information as well as the molecular packing arrangement of the molecule <b>HPMTB</b> along three dimensions. Solution-phase and solid-state fluorescence studies have revealed the existence of aggregation-induced emissive and mechanofluorochromic properties within the molecule. Detailed solution-phase photophysical investigations of <b>HPMTB</b> have revealed the existence of aggregates in a protic polar solvent (water) via the accumulation of flakes. Solid-state emission also shows the existence of reversible mechanofluorochromism in <b>HPMTB</b>. 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Development of a Dual-State Emissive Naphthalimide-Based Organic Probe: Interesting Synergistic Effects from the Solid State to the Solution Phase
Luminescent compounds have garnered significant interest for their wide range of applications in light harvesting, cell imagining, LASERs, light-emitting diodes, etc. Conventional luminescent organic molecules show their emissive properties in the solution phase; however, in the solid state, a quenching of the fluorescence intensity occurs. Researchers have been able to overcome such challenges using the phenomenon of aggregation-induced emission (AIE), which enhances the solid-state emissive properties through close packing aided by nonbonded interactions. Such molecules, conventionally referred to as AIE luminogens, are observed to show phase-exclusive emissive properties, i.e., emissive in the solid state but nonemissive in the solution phase. Such drawbacks have prompted us to investigate molecules having emissive properties in both solution and solid phase, viz., dual-state emissive molecules [dual-state emission (DSE) luminogens]. Among these, naphthalimides, owing to their versatile conformational arrangements, are of prime interest. In this article, we present the design, synthesis, structural characterization, and detailed spectroscopic studies of a naphthalimide-based luminogen molecule, 6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-(6-methoxybenzothiazol-2-yl)-1H-benzoisoquinoline-1,3(2H)-dione (HPMTB). Single-crystal X-ray diffraction studies in the solid state have provided detailed structural information as well as the molecular packing arrangement of the molecule HPMTB along three dimensions. Solution-phase and solid-state fluorescence studies have revealed the existence of aggregation-induced emissive and mechanofluorochromic properties within the molecule. Detailed solution-phase photophysical investigations of HPMTB have revealed the existence of aggregates in a protic polar solvent (water) via the accumulation of flakes. Solid-state emission also shows the existence of reversible mechanofluorochromism in HPMTB. The current work develops materials that can attain DSE and mechanofluorochromism and sets up the foundation for the development of naphthalimide-based organic molecules for use as luminescent smart materials.
期刊介绍:
The aim of Crystal Growth & Design is to stimulate crossfertilization of knowledge among scientists and engineers working in the fields of crystal growth, crystal engineering, and the industrial application of crystalline materials.
Crystal Growth & Design publishes theoretical and experimental studies of the physical, chemical, and biological phenomena and processes related to the design, growth, and application of crystalline materials. Synergistic approaches originating from different disciplines and technologies and integrating the fields of crystal growth, crystal engineering, intermolecular interactions, and industrial application are encouraged.