Light blue rigid excited-state intramolecular proton transfer organic semiconductor laser chromophores

Allison, Ilene; Mamada, Mashashi; Shukla, Atul; McGregor, Sarah K. M.; Roseli, Ras Baizureen; Gale, Innes; Rahane, Vijay P.; Moore, Evan G.; Krenske, Elizabeth H.; Jain, Nidhi; Adachi, Chihaya; Namdas, Ebinazar B.; Lo, Shih-Chun

doi:10.1039/d3tc02707d

Cited by 4 publications

(2 citation statements)

References 55 publications

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“…Excited-state proton transfer (ESPT) 1 is a fundamental process in chemistry and biology that has gained significant attention due to its diverse applications, 2 including in white light-emitting diodes (LEDs), 3 light-driven proton pumps by bacteriorhodopsin, 4 and fluorescent protein-based biosensors for cation detection. 5 From a molecular structure perspective, the ESPT process can be classified into intramolecular and intermolecular proton transfer processes (ESIntraPT and ESInterPT, Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Photochromism of phenazine-2,3-diol derivatives through excited state intermolecular proton transfer based on keto–enol tautomerization

Ohira,

Kozuka,

Kaneda

et al. 2024

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

Photochromism of phenazine-2,3-diol derivatives through excited state intermolecular proton transfer based on keto–enol tautomerization

Ohira,

Kozuka,

Kaneda

et al. 2024

Org. Biomol. Chem.

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“…Extensive research in excited-state intramolecular proton transfer (ESIPT) has revealed its essential role in various applications such as luminescent materials, [1] organic light-emitting diodes, [2,3] bioimaging probes, [4,5] photoswitches, [6,7] and molecular logic gates. [8,9] ESIPT molecules typically exist in two tautomeric forms: enol (E) and keto (K).…”

Section: Introductionmentioning

confidence: 99%

AIE‐ESIPT Photoluminescent Probe Based on 3‐(3‐Hydroxypyridin‐2‐yl)isoquinolin‐4‐ol for the Detection of Intracellular Hydrogen Peroxide

Huo,

Takayama,

Miki

et al. 2024

Chemistry A European J

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Excited‐state intramolecular proton transfer (ESIPT) molecules, which feature large Stokes shifts to avoid self‐absorption, play an essential role in photoluminescent bioimaging probes. Herein, we report the development of an ESIPT molecule 3‐(3‐hydroxypyridin‐2‐yl)isoquinolin‐4‐ol (PiQ). PiQ not only undergoes a distinct ESIPT process unlike the symmetrical 2,2′‐bipyridyl‐3,3′‐diol but also exhibits aggregation‐induced emission (AIE) characteristics. PiQ self‐assembles into aggregates with an average size of 241.0 ± 51.9 nm in aqueous solutions, leading to significantly enhanced photoluminescence. On the basis of the ESIPT and AIE characteristics of PiQ, the latter is functionalized with a hydrogen peroxide‐responsive 4‐pinacoratoborylbenzyl group (B) and a carboxylesterase‐responsive acetyl group (A) to produce a photoluminescent probe B‐PiQ‐A. The potential of PiQ for applications in bioimaging and chemical sensing is underscored by its efficient detection of both endogenous and exogenous hydrogen peroxide in living cells.

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Highly Stable Red Emissive Organic Semiconductor Materials with Low Amplified Spontaneous Emission Thresholds

Rahane,

Roseli,

Ireland

et al. 2024

Advanced Optical Materials

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Excited‐state intramolecular proton transfer (ESIPT) chromophores have attracted considerable attention as promising gain media for organic lasers, particularly in amplified spontaneous emission (ASE) due to their advantageous characteristics. These include an intrinsic four‐level photocycle, significant separation between absorption and emission spectra, and enhanced emission efficiency facilitated by aggregate‐induced emission. This study investigates the amplification of π‐conjugation in hydroxyphenyl‐benzothiazole (HBT)‐based ESIPT materials via dimerization to intensify ESIPT processes, surge absorption cross‐section, enhance optical gain, and induce a redshift in emission spectra. Computational study shows that the ESIPT processes of the new dimers proceed through single proton transfer where the second proton transfer is not accessible. While the ESIPT photocycle does not extend to both HBT moieties of the dimers, the dimers foster more efficient ESIPT processes in both solution and solid states than their parent HBT, resulting in substantial Stokes shifts (>233 nm). Moreover, both dimers exhibit enhanced solid‐state photoluminescence quantum yields, reaching up to ≈55%, and low solid‐state ASE threshold values (≈6.8 µJ cm−2) in the red region. Remarkably, the new dimers demonstrate excellent thermal and photostability with notably reduced spectral overlap compared to their parent, highlighting the potential utility of the approaches to developing new organic solid‐state laser materials.

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Light blue rigid excited-state intramolecular proton transfer organic semiconductor laser chromophores

Abstract: The effect of excited-state intramolecular proton-transfer (ESIPT) laser material rigidity on photophysical properties and amplified spontaneous emission (ASE) thresholds (EASEth) is studied.

Cited by 4 publications

References 55 publications

Photochromism of phenazine-2,3-diol derivatives through excited state intermolecular proton transfer based on keto–enol tautomerization

Photochromism of phenazine-2,3-diol derivatives through excited state intermolecular proton transfer based on keto–enol tautomerization

AIE‐ESIPT Photoluminescent Probe Based on 3‐(3‐Hydroxypyridin‐2‐yl)isoquinolin‐4‐ol for the Detection of Intracellular Hydrogen Peroxide

Highly Stable Red Emissive Organic Semiconductor Materials with Low Amplified Spontaneous Emission Thresholds

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