Design and Synthesis of a Caged Carboxylic Acid with a Donor-π-Donor Coumarin Structure: One-photon and Two-photon Uncaging Reactions Using Visible and Near-Infrared Lights

Youhei Chitose; Manabu Abe; Ko Furukawa; Jhe Yi Lin; Tzu Chau Lin; Claudine Katan

doi:10.1021/acs.orglett.7b00957

Design and Synthesis of a Caged Carboxylic Acid with a Donor-π-Donor Coumarin Structure: One-photon and Two-photon Uncaging Reactions Using Visible and Near-Infrared Lights

Youhei Chitose, Manabu Abe, Ko Furukawa, Jhe Yi Lin, Tzu Chau Lin, Claudine Katan

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

31 Citations (Scopus)

Abstract

A caged carboxylic acid with a novel two-photon (TP)-responsive donor-π-donor coumarin backbone with a quadrupolar nature was designed and synthesized in this study. The newly synthesized coumarin derivative showed a strong one-photon (OP) absorption band (ϵ ≈ 29000 cm^-1 M^-1) in the visible region (>∼400 nm). Time-dependent density functional theory calculations predicted a sizable TP absorption cross-section with a maximum at ∼650 nm significantly lager than that related to the OP absorption band. This is confirmed experimentally using TP excited fluorescence in the fs regime that leads to TP absorption cross-section of 18 and 5.6 GM at 680 and 760 nm, respectively. The OP photolysis (400 nm) and near-infrared-TP photolysis (750 nm) of the caged benzoic acid resulted in a clean formation of benzoic acid and an aldehyde.

Original language	English
Pages (from-to)	2622-2625
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.7b00957
Publication status	Published - May 19 2017
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.7b00957

Cite this

@article{8ca66b9ceb6f4487bfba312ea272bfcb,

title = "Design and Synthesis of a Caged Carboxylic Acid with a Donor-π-Donor Coumarin Structure: One-photon and Two-photon Uncaging Reactions Using Visible and Near-Infrared Lights",

abstract = "A caged carboxylic acid with a novel two-photon (TP)-responsive donor-π-donor coumarin backbone with a quadrupolar nature was designed and synthesized in this study. The newly synthesized coumarin derivative showed a strong one-photon (OP) absorption band (ϵ ≈ 29000 cm-1 M-1) in the visible region (>∼400 nm). Time-dependent density functional theory calculations predicted a sizable TP absorption cross-section with a maximum at ∼650 nm significantly lager than that related to the OP absorption band. This is confirmed experimentally using TP excited fluorescence in the fs regime that leads to TP absorption cross-section of 18 and 5.6 GM at 680 and 760 nm, respectively. The OP photolysis (400 nm) and near-infrared-TP photolysis (750 nm) of the caged benzoic acid resulted in a clean formation of benzoic acid and an aldehyde.",

author = "Youhei Chitose and Manabu Abe and Ko Furukawa and Lin, {Jhe Yi} and Lin, {Tzu Chau} and Claudine Katan",

note = "Funding Information: NMR and MS measurements were performed at N-BARD, Hiroshima University. M.A. gratefully acknowledges the financial support by a Grant- in-Aid for Science Research on Innovative Areas Stimuli-responsive Chemical Species (No. 2408) (JSPS KAKENHI Grant No. JP24109008) and JP17H0302200. T.C.L. acknowledges the financial support from the Ministry of Science and Technology (MOST), Taiwan (Grant No. MOST 105-2113-M-008-004). C.K. acknowledges the HPC resources of CINES and IDRIS under the allocations 2016-[x2016080649] made by GENCI. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = may,

day = "19",

doi = "10.1021/acs.orglett.7b00957",

language = "English",

volume = "19",

pages = "2622--2625",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Design and Synthesis of a Caged Carboxylic Acid with a Donor-π-Donor Coumarin Structure

T2 - One-photon and Two-photon Uncaging Reactions Using Visible and Near-Infrared Lights

AU - Chitose, Youhei

AU - Abe, Manabu

AU - Furukawa, Ko

AU - Lin, Jhe Yi

AU - Lin, Tzu Chau

AU - Katan, Claudine

N1 - Funding Information: NMR and MS measurements were performed at N-BARD, Hiroshima University. M.A. gratefully acknowledges the financial support by a Grant- in-Aid for Science Research on Innovative Areas Stimuli-responsive Chemical Species (No. 2408) (JSPS KAKENHI Grant No. JP24109008) and JP17H0302200. T.C.L. acknowledges the financial support from the Ministry of Science and Technology (MOST), Taiwan (Grant No. MOST 105-2113-M-008-004). C.K. acknowledges the HPC resources of CINES and IDRIS under the allocations 2016-[x2016080649] made by GENCI. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/5/19

Y1 - 2017/5/19

N2 - A caged carboxylic acid with a novel two-photon (TP)-responsive donor-π-donor coumarin backbone with a quadrupolar nature was designed and synthesized in this study. The newly synthesized coumarin derivative showed a strong one-photon (OP) absorption band (ϵ ≈ 29000 cm-1 M-1) in the visible region (>∼400 nm). Time-dependent density functional theory calculations predicted a sizable TP absorption cross-section with a maximum at ∼650 nm significantly lager than that related to the OP absorption band. This is confirmed experimentally using TP excited fluorescence in the fs regime that leads to TP absorption cross-section of 18 and 5.6 GM at 680 and 760 nm, respectively. The OP photolysis (400 nm) and near-infrared-TP photolysis (750 nm) of the caged benzoic acid resulted in a clean formation of benzoic acid and an aldehyde.

AB - A caged carboxylic acid with a novel two-photon (TP)-responsive donor-π-donor coumarin backbone with a quadrupolar nature was designed and synthesized in this study. The newly synthesized coumarin derivative showed a strong one-photon (OP) absorption band (ϵ ≈ 29000 cm-1 M-1) in the visible region (>∼400 nm). Time-dependent density functional theory calculations predicted a sizable TP absorption cross-section with a maximum at ∼650 nm significantly lager than that related to the OP absorption band. This is confirmed experimentally using TP excited fluorescence in the fs regime that leads to TP absorption cross-section of 18 and 5.6 GM at 680 and 760 nm, respectively. The OP photolysis (400 nm) and near-infrared-TP photolysis (750 nm) of the caged benzoic acid resulted in a clean formation of benzoic acid and an aldehyde.

UR - http://www.scopus.com/inward/record.url?scp=85019391712&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85019391712&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b00957

DO - 10.1021/acs.orglett.7b00957

M3 - Article

C2 - 28485152

AN - SCOPUS:85019391712

VL - 19

SP - 2622

EP - 2625

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -

Design and Synthesis of a Caged Carboxylic Acid with a Donor-π-Donor Coumarin Structure: One-photon and Two-photon Uncaging Reactions Using Visible and Near-Infrared Lights

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this