Molecular Viscosity Sensors with Two Rotators for Optimizing the Fluorescence Intensity–Contrast Trade-Off

Seung Chul Lee, Chang Lyoul Lee, Jeongyun Heo, Chan Uk Jeong, Gyeong Hui Lee, Sehoon Kim, Woojin Yoon, Hoseop Yun, Sung O. Park, Sang Kyu Kwak, Sung Ha Park, O. Pil Kwon

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A series of fluorescent molecular rotors obtained by introducing two rotational groups (“rotators”), which exhibit different rotational and electron-donating abilities, are discussed. Whereas the control molecular rotor, PH, includes a single rotator (the widely used phenyl group), the PO molecular rotors consist of two rotators (a phenyl group and an alkoxy group), which exhibit simultaneous strongly electron-donating and easy rotational abilities. Compared with the control rotor PH, PO molecular rotors exhibited one order of magnitude higher quantum yield (fluorescence intensity) and simultaneously exhibited significantly higher fluorescence contrast. These properties are directly related to the strong electron-donating ability and low energy barrier of rotation of the alkoxy group, as confirmed by dynamic fluorescence experiments and quantum chemical calculations. The PO molecular rotors exhibited two fluorescence relaxation pathways, whereas the PH molecular rotor exhibited a single fluorescence relaxation pathway. Cellular fluorescence imaging with PO molecular rotors for mapping cellular viscosity was successfully demonstrated.

Original languageEnglish
Pages (from-to)2888-2897
Number of pages10
JournalChemistry - A European Journal
Volume24
Issue number12
DOIs
Publication statusPublished - 2018 Feb 26
Externally publishedYes

Fingerprint

Viscosity
Rotors
Fluorescence
Sensors
Electrons
Optical Imaging
Energy barriers
Quantum yield
Imaging techniques
alkoxyl radical

Keywords

  • dyes/pigments
  • fluorescence
  • molecular rotors
  • sensors
  • viscosity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Molecular Viscosity Sensors with Two Rotators for Optimizing the Fluorescence Intensity–Contrast Trade-Off. / Lee, Seung Chul; Lee, Chang Lyoul; Heo, Jeongyun; Jeong, Chan Uk; Lee, Gyeong Hui; Kim, Sehoon; Yoon, Woojin; Yun, Hoseop; Park, Sung O.; Kwak, Sang Kyu; Park, Sung Ha; Kwon, O. Pil.

In: Chemistry - A European Journal, Vol. 24, No. 12, 26.02.2018, p. 2888-2897.

Research output: Contribution to journalArticle

Lee, SC, Lee, CL, Heo, J, Jeong, CU, Lee, GH, Kim, S, Yoon, W, Yun, H, Park, SO, Kwak, SK, Park, SH & Kwon, OP 2018, 'Molecular Viscosity Sensors with Two Rotators for Optimizing the Fluorescence Intensity–Contrast Trade-Off', Chemistry - A European Journal, vol. 24, no. 12, pp. 2888-2897. https://doi.org/10.1002/chem.201704036
Lee, Seung Chul ; Lee, Chang Lyoul ; Heo, Jeongyun ; Jeong, Chan Uk ; Lee, Gyeong Hui ; Kim, Sehoon ; Yoon, Woojin ; Yun, Hoseop ; Park, Sung O. ; Kwak, Sang Kyu ; Park, Sung Ha ; Kwon, O. Pil. / Molecular Viscosity Sensors with Two Rotators for Optimizing the Fluorescence Intensity–Contrast Trade-Off. In: Chemistry - A European Journal. 2018 ; Vol. 24, No. 12. pp. 2888-2897.
@article{4d19620451eb4d1a87f585f40a5966b9,
title = "Molecular Viscosity Sensors with Two Rotators for Optimizing the Fluorescence Intensity–Contrast Trade-Off",
abstract = "A series of fluorescent molecular rotors obtained by introducing two rotational groups (“rotators”), which exhibit different rotational and electron-donating abilities, are discussed. Whereas the control molecular rotor, PH, includes a single rotator (the widely used phenyl group), the PO molecular rotors consist of two rotators (a phenyl group and an alkoxy group), which exhibit simultaneous strongly electron-donating and easy rotational abilities. Compared with the control rotor PH, PO molecular rotors exhibited one order of magnitude higher quantum yield (fluorescence intensity) and simultaneously exhibited significantly higher fluorescence contrast. These properties are directly related to the strong electron-donating ability and low energy barrier of rotation of the alkoxy group, as confirmed by dynamic fluorescence experiments and quantum chemical calculations. The PO molecular rotors exhibited two fluorescence relaxation pathways, whereas the PH molecular rotor exhibited a single fluorescence relaxation pathway. Cellular fluorescence imaging with PO molecular rotors for mapping cellular viscosity was successfully demonstrated.",
keywords = "dyes/pigments, fluorescence, molecular rotors, sensors, viscosity",
author = "Lee, {Seung Chul} and Lee, {Chang Lyoul} and Jeongyun Heo and Jeong, {Chan Uk} and Lee, {Gyeong Hui} and Sehoon Kim and Woojin Yoon and Hoseop Yun and Park, {Sung O.} and Kwak, {Sang Kyu} and Park, {Sung Ha} and Kwon, {O. Pil}",
year = "2018",
month = "2",
day = "26",
doi = "10.1002/chem.201704036",
language = "English",
volume = "24",
pages = "2888--2897",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "12",

}

TY - JOUR

T1 - Molecular Viscosity Sensors with Two Rotators for Optimizing the Fluorescence Intensity–Contrast Trade-Off

AU - Lee, Seung Chul

AU - Lee, Chang Lyoul

AU - Heo, Jeongyun

AU - Jeong, Chan Uk

AU - Lee, Gyeong Hui

AU - Kim, Sehoon

AU - Yoon, Woojin

AU - Yun, Hoseop

AU - Park, Sung O.

AU - Kwak, Sang Kyu

AU - Park, Sung Ha

AU - Kwon, O. Pil

PY - 2018/2/26

Y1 - 2018/2/26

N2 - A series of fluorescent molecular rotors obtained by introducing two rotational groups (“rotators”), which exhibit different rotational and electron-donating abilities, are discussed. Whereas the control molecular rotor, PH, includes a single rotator (the widely used phenyl group), the PO molecular rotors consist of two rotators (a phenyl group and an alkoxy group), which exhibit simultaneous strongly electron-donating and easy rotational abilities. Compared with the control rotor PH, PO molecular rotors exhibited one order of magnitude higher quantum yield (fluorescence intensity) and simultaneously exhibited significantly higher fluorescence contrast. These properties are directly related to the strong electron-donating ability and low energy barrier of rotation of the alkoxy group, as confirmed by dynamic fluorescence experiments and quantum chemical calculations. The PO molecular rotors exhibited two fluorescence relaxation pathways, whereas the PH molecular rotor exhibited a single fluorescence relaxation pathway. Cellular fluorescence imaging with PO molecular rotors for mapping cellular viscosity was successfully demonstrated.

AB - A series of fluorescent molecular rotors obtained by introducing two rotational groups (“rotators”), which exhibit different rotational and electron-donating abilities, are discussed. Whereas the control molecular rotor, PH, includes a single rotator (the widely used phenyl group), the PO molecular rotors consist of two rotators (a phenyl group and an alkoxy group), which exhibit simultaneous strongly electron-donating and easy rotational abilities. Compared with the control rotor PH, PO molecular rotors exhibited one order of magnitude higher quantum yield (fluorescence intensity) and simultaneously exhibited significantly higher fluorescence contrast. These properties are directly related to the strong electron-donating ability and low energy barrier of rotation of the alkoxy group, as confirmed by dynamic fluorescence experiments and quantum chemical calculations. The PO molecular rotors exhibited two fluorescence relaxation pathways, whereas the PH molecular rotor exhibited a single fluorescence relaxation pathway. Cellular fluorescence imaging with PO molecular rotors for mapping cellular viscosity was successfully demonstrated.

KW - dyes/pigments

KW - fluorescence

KW - molecular rotors

KW - sensors

KW - viscosity

UR - http://www.scopus.com/inward/record.url?scp=85037359388&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85037359388&partnerID=8YFLogxK

U2 - 10.1002/chem.201704036

DO - 10.1002/chem.201704036

M3 - Article

AN - SCOPUS:85037359388

VL - 24

SP - 2888

EP - 2897

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 12

ER -