The effect of regioisomerism on the photophysical properties of alkylated-naphthalene liquids

Narayan, Bhawani; Nagura, Kazuhiko; Takaya, Tomohisa; Iwata, Koichi; Shinohara, Akira; Shinmori, Hideyuki; Wang, Hao; Li, Q.; Sun, Xiangnan; Li, H.; Ishihara, Shinsuke; Nakanishi, Takashi

doi:10.1039/c7cp05584f

Cited by 35 publications

(32 citation statements)

References 32 publications

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“…Moreover, such LMLs often exhibit low viscosities. For instance, the LMLs of alkylated tetrazines and alkylated naphthalenes exhibit complex viscosities (η*) in the ranges of 28–58 and 38–67 mPa • s, respectively, which are much lower than the η* of alkylated oligo( p ‐phenylenevinylene)s (0.64–34.6 Pa • s), alkylated 9,10‐diphenylanthracenes (0.28–84.0 Pa • s), alkylated pyrenes (2.3–58.0 Pa • s), and an alkylated bromonaphthalimide (0.79 Pa • s) . Such low viscous LMLs are promising for developing refreshable devices owing to their facile refilling.…”

Section: Design Principles Of Lmlsmentioning

confidence: 99%

“…Such low viscous LMLs are promising for developing refreshable devices owing to their facile refilling. However, they generally possess lower thermostability (decompose at temperatures below 275 °C) than LMLs containing larger π‐conjugated chromophores (decompose at temperatures above 350 °C).…”

Section: Design Principles Of Lmlsmentioning

confidence: 99%

“…Once enveloped by suitable side chains, various luminescent dyes can be made liquid, with their intense emission maintained in the solvent‐free neat state. To date, deep‐blue‐emitting Naphs , blue‐emitting Fluos , DPAs , OPVs , Pys , azaacenes, blue‐green‐emitting Pys and TPEs , green‐emitting OPEs , orange‐emitting TTZs , and red‐emitting BZTs have been reported.…”

Section: Enrichment Of the Functionality Of Lmlsmentioning

confidence: 99%

Section: Enrichment Of the Functionality Of Lmlsmentioning

confidence: 99%

“…Later, the alkyl chain substitution effect was systematically investigated by us. A series of regioisomeric alkylated naphthalene liquids ( Naph26 – Naph31 ) was prepared (Figure b), with Guerbet alcohol‐based branched alkyl chains of different lengths substituted at 1‐ or 2‐position of naphthalene. It was anticipated that the changes of side chain substitution pattern would alter both the electronic structure and packing modes of the naphthalene units, therefore providing a clear correlation of the molecular structure with the photophysical properties.…”

Section: Enrichment Of the Functionality Of Lmlsmentioning

confidence: 99%

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Solvent‐Free Luminous Molecular Liquids

Nakanishi

2019

Advanced Optical Materials

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Solvent‐free luminous molecular liquids (LMLs) are a new generation of soft matter which exhibit uncharged, nonvolatile, and fluidic nature and emit intense and homogeneous luminescence in the condensed state. They can be produced readily on the gram scale by modifying luminophores with bulky, flexible, and low‐melting side chains. Their performance can be facilely enriched by blending them with commercially available functional substances. Therefore, since their active optoelectronic properties were perceived a decade ago, LMLs have been regarded as promising contributing components in the burgeoning field of flexible and wearable light‐emitting devices. Recently, richer insights into LMLs have triggered various new applications. Additionally, unexpected phase behavior and photophysical properties have been discovered coincidentally. Therefore, the sensible and sophisticated molecular design principles of LMLs are still being augmented to guarantee predictable, steady, and consistent end‐use performance. This review summarizes the latest developments in LMLs, including molecular design principles, regulation and enrichment of their photophysical properties, and their versatile applications. Additionally, a prediction of the perspectives of LMLs in the near future is presented at the end.

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Section: Design Principles Of Lmlsmentioning

confidence: 99%

Section: Design Principles Of Lmlsmentioning

confidence: 99%

Section: Enrichment Of the Functionality Of Lmlsmentioning

confidence: 99%

Section: Enrichment Of the Functionality Of Lmlsmentioning

confidence: 99%

Section: Enrichment Of the Functionality Of Lmlsmentioning

confidence: 99%

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Solvent‐Free Luminous Molecular Liquids

Nakanishi

2019

Advanced Optical Materials

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Room‐Temperature Liquid Dyes

Narayan

Nakanishi

2019

Functional Organic Liquids

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A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores

Kushwaha

Stranius

et al. 2019

Advanced Science

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Liquid chromophores constitute a rare but intriguing class of molecules that are in high demand for the design of luminescent inks, liquid semiconductors, and solar energy storage materials. The most common way to achieve liquid chromophores involves the introduction of long alkyl chains, which, however, significantly reduces the chromophore density. Here, strategy is presented that allows for the preparation of liquid chromophores with a minimal increase in molecular weight, using the important class of perylenes as an example. Two synergistic effects are harnessed: (1) the judicious positioning of short alkyl substituents, and (2) equimolar mixing, which in unison results in a liquid material. A series of 1‐alkyl perylene derivatives is synthesized and it is found that short ethyl or butyl chains reduce the melting temperature from 278 °C to as little as 70 °C. Then, two low‐melting derivatives are mixed, which results in materials that do not crystallize due to the increased configurational entropy of the system. As a result, liquid chromophores with the lowest reported molecular weight increase compared to the neat chromophore are obtained. The mixing strategy is readily applicable to other π‐conjugated systems and, hence, promises to yield a wide range of low molecular weight liquid chromophores.

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The effect of regioisomerism on the photophysical properties of alkylated-naphthalene liquids

Cited by 35 publications

References 32 publications

Solvent‐Free Luminous Molecular Liquids

Solvent‐Free Luminous Molecular Liquids

Room‐Temperature Liquid Dyes

A Record Chromophore Density in High‐Entropy Liquids of Two Low‐Melting Perylenes: A New Strategy for Liquid Chromophores

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