A new pH sensitive fluorescent and white light emissive material through controlled intermolecular charge transfer

Park, Y. I.; Postupna, Olena; Zhugayevych, Andriy; Shin, Hoon−Kyu; Kim, B.; Yen, Hung‐Ju; Cheruku, Pradeep; Martinez, Jennifer S.; Park, J. W.; Tretiak, Sergei; Wang, H.-L.

doi:10.1039/c4sc01911c

Cited by 92 publications

(95 citation statements)

References 59 publications

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“…Aggregation effects cause excimer emission which is strongly red or blue shifted depending on the substituent and are not captured by ESMD of single molecules [25,26]. No data exists yet exists for solvatochromic shifts in these molecules which is completely free of aggregation effects.…”

Section: Resultsmentioning

confidence: 94%

“…Nonetheless, experiments from Refs. [25,26] performed with varied solvents suggest that the solvatochromic shifts without aggregation effects are larger in fluorescence than in absorption, approximately 0.2 eV and 0.05-0.1 eV, respectively. These observations are in general agreement with the simulations and the predicted shifts are of reasonable magnitude for conjugated organic molecules [1,26].…”

Section: Resultsmentioning

confidence: 95%

“…Direct comparison with experiment is difficult due to aggregation effects [25,26]. Aggregation effects cause excimer emission which is strongly red or blue shifted depending on the substituent and are not captured by ESMD of single molecules [25,26].…”

Section: Resultsmentioning

confidence: 98%

“…This class of conjugated materials is rapidly evolving in applications such as molecular electronics and nanotechnology or as photovoltaic and electrochromic devices [24][25][26]. The specific molecules studied here have been implicated as excellent candidates for lightemitting diodes, showing varied emission energies ranging across the optical spectrum [25,26].…”

Section: Introductionmentioning

confidence: 98%

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Simulations of fluorescence solvatochromism in substituted PPV oligomers from excited state molecular dynamics with implicit solvent

Bjorgaard

Nelson

Kalinin

et al. 2015

Chemical Physics Letters

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a b s t r a c tAn efficient method of treating solvent effects in excited state molecular dynamics (ESMD) is implemented and tested by exploring the solvatochromic effects in substituted p-phenylene vinylene oligomers. A continuum solvent model is used which has very little computational overhead. This allows simulations of ESMD with solvent effects on the scale of hundreds of picoseconds for systems of up to hundreds of atoms. At these time scales, solvatochromic shifts in fluoresence spectra can be described. Solvatochromic shifts in absorption and fluorescence spectra from ESMD are compared with time-dependent density functional theory calculations and experiments.

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 98%

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Simulations of fluorescence solvatochromism in substituted PPV oligomers from excited state molecular dynamics with implicit solvent

Bjorgaard

Nelson

Kalinin

et al. 2015

Chemical Physics Letters

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“…The pK a of this OPPV has been previously estimated to be 3.3−4.0. 15 We found that, at each pH, the emission spectrum of the gel-immobilized OPPV was distinct from that of free OPPV ( Figure 5). The fluorescence spectra were collected at 4°C upon excitation at 390 nm, the wavelength where both free and gel-adsorbed OPPV displays maximum absorption across the temperatures and pHs used in this study.…”

Section: Acs Biomaterials Science and Engineeringmentioning

confidence: 93%

Stimuli-Responsive Genetically Engineered Polymer Hydrogel Demonstrates Emergent Optical Responses

Balog

Ghosh

Park

et al. 2016

ACS Biomater. Sci. Eng.

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Biopolymer-based optical hydrogels represent an emerging class of materials with potential applications in biocompatible integrated optoelectronic devices, bioimaging applications, and stretchable/flexible photonics. We have synthesized stimuli-responsive three-dimensional hydrogels from genetically engineered elastin-like polymers (ELPs) and have loaded these hydrogels with an amine-containing pphenylenevinylene oligomer (OPPV) derivative featuring highly tunable, environmentally sensitive optical properties. The composite ELP/OPPV hydrogels exhibit both pH-and temperature-dependent fluorescence emission, from which we have characterized a unique optical behavior that emerged from OPPV within the hydrogel environment. By systematic comparison with free OPPV in solution, our results suggest that this distinct behavior is due to local electronic effects arising from interactions between the hydrophobic ELP microenvironment and the nonprotonated OPPV species at pH 7 or higher. KEYWORDS: conjugated oligomer, composite material, optically active material, photoluminescence, polymeric material, stimuli-responsive material, genetically encoded ■ INTRODUCTIONProtein-based polymers are an exciting option for future materials applications because they are sustainable, biodegradable, and can be designed at the DNA level, affording a degree of precision not attainable through conventional polymer synthesis. Additionally, through natural selection, proteins have evolved desirable materials properties that can be manipulated for specific applications. For example, elastin-like polymers (ELPs) are based on the vertebrate protein elastin, which is a specialized extracellular matrix protein that confers mechanical properties such as extensibility and resilience to our connective tissue. Unlike typical globular proteins, which have a biochemically heterogeneous composition leading to distinct 3D folds, elastin contains a series of pentameric (VPGXG) amino acid repeats that underlie its extraordinary elasticity. 1 In aqueous environments, ELPs composed primarily of these VPGXG repeats exhibit reversible coacervation that depends upon temperature and ionic strength. 1 This same stimuli-responsive behavior can be manifested within the 3D polymer network of a hydrogel. 2 Upon heating, ELP gels condense in volume, expel water, and become opaque. Upon cooling, the gels swell, reabsorb water molecules, and become transparent. This volume shrinkage/expansion process is reversible and can be designed at the molecular level to occur in physiologically and experimentally practical temperature ranges at the macroscopic level. ELPs have shown promise in applications such as drug delivery, coatings for implants, and hydrogels for tissue engineering. 3−5 However, despite their appealing properties, there has been limited research into the integration of ELPs with optical or electronic materials, and none of this past work has taken advantage of ELP hydrogel elasticity and stimuliresponsiveness for optically active "smart" materials applications...

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3‐Bromo‐ N,N,N ‐trimethylanilinium Iodide (1:1)

Reid

2022

Encyclopedia of Reagents for Organic Synthesis

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A new pH sensitive fluorescent and white light emissive material through controlled intermolecular charge transfer

Abstract: Fabrication of a unique white light LED from a stimuli-responsive organic molecule is reported. Emission properties are dominated by the pH of the solution through intermolecular charge transfer.

Cited by 92 publications

References 59 publications

Simulations of fluorescence solvatochromism in substituted PPV oligomers from excited state molecular dynamics with implicit solvent

Simulations of fluorescence solvatochromism in substituted PPV oligomers from excited state molecular dynamics with implicit solvent

Stimuli-Responsive Genetically Engineered Polymer Hydrogel Demonstrates Emergent Optical Responses

3‐Bromo‐ N,N,N ‐trimethylanilinium Iodide (1:1)

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