pi-Extended Coumarins Derived with Nonhydrolyzable Iminophosphoranes as Two-Photon-Excited Fluorophores

Liang-Yu Hsia; Hsin-Ni Chen; Chun-Hao Chiang; Ming-Yang Hung; Hao-Keng Wei; Chih-Wei Luo; Ming-Yu Kuo; Shun-Yuan Luo; Chih-Chien Chu

doi:10.1021/acs.joc.0c00901

pi-Extended Coumarins Derived with Nonhydrolyzable Iminophosphoranes as Two-Photon-Excited Fluorophores

Liang-Yu Hsia, Hsin-Ni Chen, Chun-Hao Chiang, Ming-Yang Hung, Hao-Keng Wei, Chih-Wei Luo, Ming-Yu Kuo, Shun-Yuan Luo^*, Chih-Chien Chu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

Novel coumarin-iminophosphorane (IPP) fluorophores that have stable resonance contributions from aza-ylides were formed by using the nonhydrolysis Staudinger reaction. The N=P formation reaction kinetics obey the conventional Staudinger reaction. The absorption and emission profiles of the coumarin-IPP derivatives can be fine-tuned: an electron-donating group at PPh3 enhances absorption and fluorescence, whereas an electron-withdrawing group at C-3 drives absorption and emission peaks toward blue-light wavelengths. Two-photon adsorption, accompanied by anti-Stokes fluorescence, is achieved under near-infrared femtosecond laser excitation.

Original language	English
Pages (from-to)	9361-9366
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	85
Issue number	14
DOIs	https://doi.org/10.1021/acs.joc.0c00901
State	Published - 17 Jul 2020

Keywords

STAUDINGER REACTION
AZIDES
ACID

Access to Document

10.1021/acs.joc.0c00901

Cite this

@article{c8680f48e73e42e39cce40ac576f8759,

title = "pi-Extended Coumarins Derived with Nonhydrolyzable Iminophosphoranes as Two-Photon-Excited Fluorophores",

abstract = "Novel coumarin-iminophosphorane (IPP) fluorophores that have stable resonance contributions from aza-ylides were formed by using the nonhydrolysis Staudinger reaction. The N=P formation reaction kinetics obey the conventional Staudinger reaction. The absorption and emission profiles of the coumarin-IPP derivatives can be fine-tuned: an electron-donating group at PPh3 enhances absorption and fluorescence, whereas an electron-withdrawing group at C-3 drives absorption and emission peaks toward blue-light wavelengths. Two-photon adsorption, accompanied by anti-Stokes fluorescence, is achieved under near-infrared femtosecond laser excitation.",

keywords = "STAUDINGER REACTION, AZIDES, ACID",

author = "Liang-Yu Hsia and Hsin-Ni Chen and Chun-Hao Chiang and Ming-Yang Hung and Hao-Keng Wei and Chih-Wei Luo and Ming-Yu Kuo and Shun-Yuan Luo and Chih-Chien Chu",

year = "2020",

month = jul,

day = "17",

doi = "10.1021/acs.joc.0c00901",

language = "English",

volume = "85",

pages = "9361--9366",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - pi-Extended Coumarins Derived with Nonhydrolyzable Iminophosphoranes as Two-Photon-Excited Fluorophores

AU - Hsia, Liang-Yu

AU - Chen, Hsin-Ni

AU - Chiang, Chun-Hao

AU - Hung, Ming-Yang

AU - Wei, Hao-Keng

AU - Luo, Chih-Wei

AU - Kuo, Ming-Yu

AU - Luo, Shun-Yuan

AU - Chu, Chih-Chien

PY - 2020/7/17

Y1 - 2020/7/17

N2 - Novel coumarin-iminophosphorane (IPP) fluorophores that have stable resonance contributions from aza-ylides were formed by using the nonhydrolysis Staudinger reaction. The N=P formation reaction kinetics obey the conventional Staudinger reaction. The absorption and emission profiles of the coumarin-IPP derivatives can be fine-tuned: an electron-donating group at PPh3 enhances absorption and fluorescence, whereas an electron-withdrawing group at C-3 drives absorption and emission peaks toward blue-light wavelengths. Two-photon adsorption, accompanied by anti-Stokes fluorescence, is achieved under near-infrared femtosecond laser excitation.

AB - Novel coumarin-iminophosphorane (IPP) fluorophores that have stable resonance contributions from aza-ylides were formed by using the nonhydrolysis Staudinger reaction. The N=P formation reaction kinetics obey the conventional Staudinger reaction. The absorption and emission profiles of the coumarin-IPP derivatives can be fine-tuned: an electron-donating group at PPh3 enhances absorption and fluorescence, whereas an electron-withdrawing group at C-3 drives absorption and emission peaks toward blue-light wavelengths. Two-photon adsorption, accompanied by anti-Stokes fluorescence, is achieved under near-infrared femtosecond laser excitation.

KW - STAUDINGER REACTION

KW - AZIDES

KW - ACID

U2 - 10.1021/acs.joc.0c00901

DO - 10.1021/acs.joc.0c00901

M3 - Article

SN - 0022-3263

VL - 85

SP - 9361

EP - 9366

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

pi-Extended Coumarins Derived with Nonhydrolyzable Iminophosphoranes as Two-Photon-Excited Fluorophores

Abstract

Keywords

Access to Document

Fingerprint

Cite this