Molecular Rotors as Fluorescent Viscosity Sensors: Molecular Design, Polarity Sensitivity, Dipole Moments Changes, Screening Solvents, and Deactivation Channel of the Excited States

Zhou, Fuke; Shao, Jingyin; Yang, Yunjie; Zhao, Jianzhang; Guo, Huimin; Li, Xiaolian; Ji, Shaomin; Zhang, Zongying

doi:10.1002/ejoc.201100606

Cited by 97 publications

(31 citation statements)

References 56 publications

(140 reference statements)

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“…[26][27][28] FMRs have become rather popular in the last 5-10 years thanks to their easy applicability as non-mechanical viscosity sensors, tools for protein characterization, and local microviscosity imaging. [29][30][31][32][33][34][35][36][37] Remarkably, their sensitivity towards viscosity and viscosity changes has reached a precision comparable to that of commercial mechanical rheometers with shorter measurement time.…”

Section: Introductionmentioning

confidence: 99%

Reversible vapochromic response of polymer films doped with a highly emissive molecular rotor

et al. 2014

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We report on a new vapochromic system suitable for sensing volatile organic compounds (VOCs) based on polymer films doped with 4-(diphenylamino)phthalonitrile (DPAP), a fluorescent molecular rotor sensitive to both solvent polarity and viscosity. Poly(methyl methacrylate) (PMMA) and polycarbonate (PC) films containing small amounts of DPAP (#0.1 wt%) were prepared and exposed to saturated atmospheres of different VOCs. DPAP/PMMA films show a good and reversible vapochromism when exposed to VOCs with high polarity index and favourable interaction with polymer matrices such as THF, CHCl 3 , and acetonitrile. Analogously, DPAP/PC films exposed to polar and highly polymer-interacting solvents, that is, toluene, THF, and CHCl 3 , show a gradual decrease and red-shift of the emission. In contrast to DPAP/ PMMA films, an unexpected increase and further red-shift of fluorescence are observed at longer exposure times as a consequence of an irreversible, solvent-induced crystallization process of PC. The vapochromism of DPAP-doped films is rationalized on the basis of alterations of the rotor intramolecular motion and polarity effects stemming from the environment, which, in concert, influence the deactivation pathways of the DPAP intramolecular charge transfer state. Overall, the present results support the use of DPAP-enriched plastic films as a new chromogenic material suitable for the detection of VOCs.

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Section: Introductionmentioning

confidence: 99%

Reversible vapochromic response of polymer films doped with a highly emissive molecular rotor

et al. 2014

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“…where h is the viscosity of the medium in which the molecular rotors are present, a is a constant, and x is the viscosity sensitivity of the molecular rotor [11]. Therefore, for a molecular rotor, the dependence of the fluorescence intensity upon molecular absorption and viscosity should be expressed as:…”

Section: Resultsmentioning

confidence: 99%

The role of viscosity in the fluorescence behavior of the diesel/biodiesel blends

Caires¹,

Scherer²,

Souza³

et al. 2014

Renewable Energy

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a b s t r a c tRecently, the potentiality of fluorescence spectroscopy to be used in the quantification of biodiesel content in diesel/biodiesel blends (DBB) was demonstrated. However, the source of the fluorescence dependence of the DBB with biodiesel concentration remains unanswered. In the present paper, a close analysis of the optical properties of the DBB was performed over a wide composition range. The findings suggest that the alterations in the fluorescence intensity can be accounted for only after taking into account changes in viscosity as well as absorbance, in a model where the fluorophores were considered as molecular rotors.

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“…Recently, we showed that the acetylene bond can be used to extend the absorption/emission wavelengths of the rotors. [21] However, we found that the sensitivity of the resulting rotors to viscosity was reduced. Thus, we set out to explore another strategy to improve the photophysical properties of the rotors.…”

Section: Design Of the Fluorescent Molecular Rotorsmentioning

confidence: 94%

Thiophene‐Inserted Aryl–Dicyanovinyl Compounds: The Second Generation of Fluorescent Molecular Rotors with Significantly Redshifted Emission and Large Stokes Shift

Shao

et al. 2011

Eur J Org Chem

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Fluorescent molecular rotors can be used as molecular sensors for the viscosity of a microenvironment. However, these molecular rotors are limited to 9‐(dicyanovinyl)julolidine (DCVJ) and a few derivatives. Furthermore, these traditional rotors show short absorption/emission wavelengths and small Stokes shifts. To address these drawbacks, we have developed a small library of new molecular rotors for viscosity sensing, prepared by incorporating a thiophene unit into the conventional fluorescent molecular rotors with the aim of accessing molecular rotors with redshifted excitation/emission wavelengths and larger Stokes shifts compared with the known rotors. The new rotors show substantially improved photophysical properties. For example, rotor 4 shows absorption/emission wavelengths of 559/697 nm, respectively, and a very large Stokes shift of 138 nm compared with the absorption/emission wavelengths (465/503 nm) and very small Stokes shift (38 nm) of the traditional fluorescent molecular rotor DCVJ. The photophysical properties of the rotors were rationalized by DFT calculations.

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Molecular Rotors as Fluorescent Viscosity Sensors: Molecular Design, Polarity Sensitivity, Dipole Moments Changes, Screening Solvents, and Deactivation Channel of the Excited States

Cited by 97 publications

References 56 publications

Reversible vapochromic response of polymer films doped with a highly emissive molecular rotor

Reversible vapochromic response of polymer films doped with a highly emissive molecular rotor

The role of viscosity in the fluorescence behavior of the diesel/biodiesel blends

Thiophene‐Inserted Aryl–Dicyanovinyl Compounds: The Second Generation of Fluorescent Molecular Rotors with Significantly Redshifted Emission and Large Stokes Shift

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