Circularly Polarized Luminescence from Simple Organic Molecules

Sánchez‐Carnerero, Esther M.; Agarrabeitia, Antonia R.; Moreno, Florencio; Maroto, Beatriz Lora; Muller, Gilles; Ortiz, María J.; Cerero, Santiago de la Moya

doi:10.1002/chem.201501178

Cited by 830 publications

(613 citation statements)

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“…2 The g em values for 2 and 4 were «3.6 © 10 ¹4 « and «1.2 © 10 ¹3 «, respectively. The CPL spectra shown in Figure 3 were mirror images of each other.…”

Section: ¹4mentioning

confidence: 97%

“…1 Although CPL spectroscopy is a relatively new technique, a pioneering review was published as early as in 1977. 2 Currently, CPL is regarded as an important chiroptical technique. The applications of CPL have shifted from the analytical chemistry of biological chiral molecules 2 to advanced science using polarized light, such as three-dimensional displays and quantum computing.…”

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confidence: 99%

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π-Expanded Axially Chiral Biaryls and Their Emissions: Molecular Design, Syntheses, Optical Resolution, Absolute Configuration, and Circularly Polarized Luminescence of 1,1′-Bipyrene-2,2′-diols

et al. 2015

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Axially chiral biaryls based on pyrene, 1,1¤-bipyrene-2,2¤-diol derivatives 2, were designed and synthesized from 2-hydroxypyrene. Simple optical resolution was carried out and the absolute configuration was determined by diffraction study. Title compounds 2 and corresponding menthylcarbonate 4 showed clear circularly polarized luminescence (CPL) spectra. The degree of dimensionless Kuhn's anisotropy in the photoexcited state («g em «) of 2 and 4 were ca. 3.6 © 10 ¹4 and ca. 1.2 © 10 ¹3, respectively. Noteworthy properties were as follows: 1) high fluorescent quantum yields of 2 and 4, 0.57 and 0.80, respectively, in marked contrast to that of BINOL, 0.04 and 2) bathochromic shifts of CPL .Circularly polarized luminescence (CPL) is luminescence emitted by a chiral molecule. Because of the high sensitivity of steady-state luminescence, CPL spectroscopy has attracted much attention, particularly in the analysis and evaluation of naturally occurring chiral chromophores, such as chlorophyll (vide infra).1 Although CPL spectroscopy is a relatively new technique, a pioneering review was published as early as in 1977.2 Currently, CPL is regarded as an important chiroptical technique. The applications of CPL have shifted from the analytical chemistry of biological chiral molecules 2 to advanced science using polarized light, such as three-dimensional displays and quantum computing. 3CPL spectroscopy has flourished under the watch of physical chemists. However, the lack of a standard molecule having a large quantum yield (Φ fl ) and a large dimensionless Kuhn's anisotropy in the photoexcited state («g em «) (vide infra), 2 has hindered the development of new materials for CPL. Although 1,1¤-binaphthalen-2,2¤-diol (BINOL) 1 (Chart 1) and its corresponding derivatives are well used in this research field, Φ fl and g em are small (vide infra). In this study, our aim was to design a standard molecule for CPL spectroscopy. The expansion of the π-electronic system seemed to be the most promising strategy, i.e., replacement of the naphthalene moiety of BINOL with other π-expanded polycyclic aromatic hydrocarbons (PAHs). Generally, the expansion of the π-electronic system induces 1) a small HOMOLUMO gap and a resultant low excitation energy, 2) an increase in the fluorescence lifetime, 3) a low redox potential, and so on. 4 These properties are preferred for advanced materials. We focused on pyrene as PAH because it showed strong emission, long lifetime, and high quantum yield, making it one of the standard molecules for photochemistry. 5,6 We designed 1,1¤-bipyrene-2,2¤-diol 2, a pyrene-based axially chiral molecule, with a eye to improving the chiroptical properties of BINOLs.Optically pure title compounds 2 and reference 5 were prepared according to Scheme 1. 7 The issues to be addressed were 1) the solubility improvement of 2 and 2) optical resolution. PAHs are notorious for their poor solubilities and our targets 2, dimers of pyrene, ought to be sparingly soluble materials. To solve this problem, a tertbutyl group was intro...

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“…2 The g em values for 2 and 4 were «3.6 © 10 ¹4 « and «1.2 © 10 ¹3 «, respectively. The CPL spectra shown in Figure 3 were mirror images of each other.…”

Section: ¹4mentioning

confidence: 97%

mentioning

confidence: 99%

π-Expanded Axially Chiral Biaryls and Their Emissions: Molecular Design, Syntheses, Optical Resolution, Absolute Configuration, and Circularly Polarized Luminescence of 1,1′-Bipyrene-2,2′-diols

et al. 2015

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“…The CPL studies on small, nonpolymeric, and nonaggregated organic molecules were summarized in a recent review by de la Moya and co-workers. 8 In that article, the authors explain the design strategy for CPL systems with enhanced fluorescence quantum yields, but the low g lum value (3 × 10 −2 being the highest value reported) remained the limiting factor for simple organic chiral molecules. In contrast, we focus on the approaches adopted by researchers for effectively enhancing the luminescence dissymmetry in chiral organic molecules.…”

mentioning

confidence: 99%

Circularly Polarized Luminescence in Chiral Molecules and Supramolecular Assemblies

Kumar

Nakashima

Kawai

2015

J. Phys. Chem. Lett.

606

373

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Circularly polarized luminescence, or CPL, is a luminescence phenomenon that provides the differential emission intensity of right and left circularly polarized light, thereby providing information on the excited state properties of the chiral molecular systems. In recent years, there has been a growing interest toward the development of organic chromophores capable of circularly polarized emission due to their potential applications in sensors, asymmetric synthesis as well as display and optical storage devices. The major drawback with organic molecules is the low dissymmetric factors exhibited by these systems. One of the recent strategies adopted for the improvement in luminescence dissymmetry of organic systems is through the controlled self-assembly of chromophores. In this Perspective, we highlight the recent experimental and theoretical developments in the field of chiral organic chromophoric systems and their self-assembly, that has produced promising results toward the enhancement of glum values in CPL.

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“…Sources directly emitting circularly polarized light (CP) [132][133][134] can be of great interest in many fields, such us quantum computing, [135] optical communication for spintronics, [136] bioresponsive imaging. [137] Generally, non-polarized light is converted in CP light using filters or with more complex systems architectures, [138] which often lead to a loss in brightness.…”

Section: Applications To Organic Light Emission Diodes Technologymentioning

confidence: 99%

Materials and 3D Designs of Helix Nanostructures for Chirality at Optical Frequencies

Passaseo

Esposito

Cuscunà

et al. 2017

Advanced Optical Materials

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The capability to fully control the chiro‐optical properties of metamaterials has drawn considerable attention due to developments in metamaterial fabrication techniques and a deeper understanding of the light–matter interaction, enabling a number of applications from integrated photonics to life sciences. From simple geometrical studies on single helix shaped metamaterials, both the design complexity and nanofabrication capability are steadily increasing allowing to extend their properties to the visible regime and beyond. In this work, helix‐shaped micro‐ and nanostructures are reviewed, which have the possibility to modulate their optical response in the linear regime at optical frequencies by spatial arrangement or by constitutive material. An overview of different theories describing the general optical operation of chiral media and a discussion on experimental results obtained by the state‐of‐the‐art helix structures realized by different fabrication techniques is provided. Finally, advanced designs for improved functionality envisaged to match practical applications or to enable new optical multifunctionalities are compared. Even if many applications have been envisaged only theoretically, the continuous effort and progress shown by the research community engaged in this field suggests that helical chiral metamaterials could represent a disruptive breakthrough for advanced optical devices.

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Circularly Polarized Luminescence from Simple Organic Molecules

Cited by 830 publications

References 93 publications

π-Expanded Axially Chiral Biaryls and Their Emissions: Molecular Design, Syntheses, Optical Resolution, Absolute Configuration, and Circularly Polarized Luminescence of 1,1′-Bipyrene-2,2′-diols

π-Expanded Axially Chiral Biaryls and Their Emissions: Molecular Design, Syntheses, Optical Resolution, Absolute Configuration, and Circularly Polarized Luminescence of 1,1′-Bipyrene-2,2′-diols

Circularly Polarized Luminescence in Chiral Molecules and Supramolecular Assemblies

Materials and 3D Designs of Helix Nanostructures for Chirality at Optical Frequencies

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