Singlet oxygen-responsive photorelease of tyramine

Dong Yeun Jeong; Seung Yeon Yi; Youngmin You

doi:10.1002/bkcs.12385

Singlet oxygen-responsive photorelease of tyramine

Dong Yeun Jeong, Seung Yeon Yi, Youngmin You

Department of Chemical Engineering & Materials Science

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

1 Scopus citations

Abstract

A system capable of photoreleasing tyramine has been developed. The photodonor system consists of an isoindole cage of tyramine and a biscyclometalated Ir(III) complex singlet oxygen (¹O₂) photosensitizer. Photoirradiation at a wavelength of 365 nm produces tyramine, as evidenced by mass spectrometry and ¹H NMR spectroscopy. The photorelease proceeds through two steps involving the formation of a Diels–Alder-type [2 + 4] cycloadduct of ¹O₂, followed by the slow and spontaneous decomposition of the adduct into tyramine and 2-benzoylbenzophenon.

Original language	English
Pages (from-to)	1497-1500
Number of pages	4
Journal	Bulletin of the Korean Chemical Society
Volume	42
Issue number	11
DOIs	https://doi.org/10.1002/bkcs.12385
State	Published - Nov 2021

Bibliographical note

Funding Information:
This work was supported by the Midcareer Research Program (NRF‐2019R1A2C2003969).

Publisher Copyright:
© 2021 Korean Chemical Society, Seoul & Wiley-VCH GmbH

Keywords

iridium complex
photocage
photodelivery
singlet oxygen
tyramine

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10.1002/bkcs.12385

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title = "Singlet oxygen-responsive photorelease of tyramine",

abstract = "A system capable of photoreleasing tyramine has been developed. The photodonor system consists of an isoindole cage of tyramine and a biscyclometalated Ir(III) complex singlet oxygen (1O2) photosensitizer. Photoirradiation at a wavelength of 365 nm produces tyramine, as evidenced by mass spectrometry and 1H NMR spectroscopy. The photorelease proceeds through two steps involving the formation of a Diels–Alder-type [2 + 4] cycloadduct of 1O2, followed by the slow and spontaneous decomposition of the adduct into tyramine and 2-benzoylbenzophenon.",

keywords = "iridium complex, photocage, photodelivery, singlet oxygen, tyramine",

author = "Jeong, {Dong Yeun} and Yi, {Seung Yeon} and Youngmin You",

note = "Funding Information: This work was supported by the Midcareer Research Program (NRF‐2019R1A2C2003969). Publisher Copyright: {\textcopyright} 2021 Korean Chemical Society, Seoul & Wiley-VCH GmbH",

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doi = "10.1002/bkcs.12385",

language = "English",

volume = "42",

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journal = "Bulletin of the Korean Chemical Society",

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T1 - Singlet oxygen-responsive photorelease of tyramine

AU - Jeong, Dong Yeun

AU - Yi, Seung Yeon

AU - You, Youngmin

PY - 2021/11

Y1 - 2021/11

N2 - A system capable of photoreleasing tyramine has been developed. The photodonor system consists of an isoindole cage of tyramine and a biscyclometalated Ir(III) complex singlet oxygen (1O2) photosensitizer. Photoirradiation at a wavelength of 365 nm produces tyramine, as evidenced by mass spectrometry and 1H NMR spectroscopy. The photorelease proceeds through two steps involving the formation of a Diels–Alder-type [2 + 4] cycloadduct of 1O2, followed by the slow and spontaneous decomposition of the adduct into tyramine and 2-benzoylbenzophenon.

AB - A system capable of photoreleasing tyramine has been developed. The photodonor system consists of an isoindole cage of tyramine and a biscyclometalated Ir(III) complex singlet oxygen (1O2) photosensitizer. Photoirradiation at a wavelength of 365 nm produces tyramine, as evidenced by mass spectrometry and 1H NMR spectroscopy. The photorelease proceeds through two steps involving the formation of a Diels–Alder-type [2 + 4] cycloadduct of 1O2, followed by the slow and spontaneous decomposition of the adduct into tyramine and 2-benzoylbenzophenon.

KW - iridium complex

KW - photocage

KW - photodelivery

KW - singlet oxygen

KW - tyramine

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DO - 10.1002/bkcs.12385

M3 - Article

AN - SCOPUS:85113412953

SN - 0253-2964

VL - 42

SP - 1497

EP - 1500

JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 11

ER -

Singlet oxygen-responsive photorelease of tyramine

Abstract

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Keywords

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