Two-Photon-Absorption Properties of Pyrene-Based Dipolar D-π-A Fluorophores

Chuan Zeng Wang; Ruoyao Zhang; Koya Sakaguchi; Xing Feng; Xiaoqiang Yu; Mark R.J. Elsegood; Simon J. Teat; Carl Redshaw; Takehiko Yamato

doi:10.1002/cptc.201800053

Two-Photon-Absorption Properties of Pyrene-Based Dipolar D-π-A Fluorophores

Chuan Zeng Wang, Ruoyao Zhang, Koya Sakaguchi, Xing Feng^*, Xiaoqiang Yu, Mark R.J. Elsegood, Simon J. Teat, Carl Redshaw, Takehiko Yamato^*

^*Corresponding author for this work

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

19 Citations (Scopus)

Abstract

Two-photon absorption (TPA) properties of pyrene-based derivatives are rare as a result of the limited number of controllable synthetic methods to prepare them. However, these materials are in great demand given their potential practical application in photics and biological imaging. Herein, we present a set of pyrene-based dipolar donor-π-acceptor (D-π-A) fluorophores with a wide-range of color tuning and large TPA cross-sections (up to 2200 GM at 780 nm) by regioselective substitution at the 1,3- and 6,8-positions under the perspective of theoretical analysis. The linear and nonlinear optical properties of these compounds have been studied. The near-identical emission wavelengths between the two-photon-excited fluorescence (TPEF) and one-photon excited fluorescence (OPEF) indicated that they are generated from the same fluorescent excited state by either one- or two-photon excitation. With the exception of the strong donor [N(CH₃)₂] appended fluorophore, the TPEF exhibited a large red-shift compared with the OPEF spectra as a result of the complicated working mechanisms in operation, including intramolecular charge transfer (ICT) and twisted intramolecular charge transfer (TICT). All fluorophores exhibit high two-photon cross-sections (or two-photon brightness, δΦ), especially for 1348 GM, which indicated that these materials can be used as colorants for probe and bioimaging applications.

Original language	English
Pages (from-to)	749-756
Number of pages	8
Journal	ChemPhotoChem
Volume	2
Issue number	8
DOIs	https://doi.org/10.1002/cptc.201800053
Publication status	Published - 1 Aug 2018
Externally published	Yes

Keywords

charge transfer
dipolar molecules
donor–acceptor systems
pyrene
two-photon absorption

Access to Document

10.1002/cptc.201800053

Cite this

@article{04703f0403e54da7aba9d6fe981854eb,

title = "Two-Photon-Absorption Properties of Pyrene-Based Dipolar D-π-A Fluorophores",

abstract = "Two-photon absorption (TPA) properties of pyrene-based derivatives are rare as a result of the limited number of controllable synthetic methods to prepare them. However, these materials are in great demand given their potential practical application in photics and biological imaging. Herein, we present a set of pyrene-based dipolar donor-π-acceptor (D-π-A) fluorophores with a wide-range of color tuning and large TPA cross-sections (up to 2200 GM at 780 nm) by regioselective substitution at the 1,3- and 6,8-positions under the perspective of theoretical analysis. The linear and nonlinear optical properties of these compounds have been studied. The near-identical emission wavelengths between the two-photon-excited fluorescence (TPEF) and one-photon excited fluorescence (OPEF) indicated that they are generated from the same fluorescent excited state by either one- or two-photon excitation. With the exception of the strong donor [N(CH3)2] appended fluorophore, the TPEF exhibited a large red-shift compared with the OPEF spectra as a result of the complicated working mechanisms in operation, including intramolecular charge transfer (ICT) and twisted intramolecular charge transfer (TICT). All fluorophores exhibit high two-photon cross-sections (or two-photon brightness, δΦ), especially for 1348 GM, which indicated that these materials can be used as colorants for probe and bioimaging applications.",

keywords = "charge transfer, dipolar molecules, donor–acceptor systems, pyrene, two-photon absorption",

author = "Wang, {Chuan Zeng} and Ruoyao Zhang and Koya Sakaguchi and Xing Feng and Xiaoqiang Yu and Elsegood, {Mark R.J.} and Teat, {Simon J.} and Carl Redshaw and Takehiko Yamato",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = aug,

day = "1",

doi = "10.1002/cptc.201800053",

language = "English",

volume = "2",

pages = "749--756",

journal = "ChemPhotoChem",

issn = "2367-0932",

publisher = "Wiley-VCH Verlag",

number = "8",

}

TY - JOUR

T1 - Two-Photon-Absorption Properties of Pyrene-Based Dipolar D-π-A Fluorophores

AU - Wang, Chuan Zeng

AU - Zhang, Ruoyao

AU - Sakaguchi, Koya

AU - Feng, Xing

AU - Yu, Xiaoqiang

AU - Elsegood, Mark R.J.

AU - Teat, Simon J.

AU - Redshaw, Carl

AU - Yamato, Takehiko

PY - 2018/8/1

Y1 - 2018/8/1

N2 - Two-photon absorption (TPA) properties of pyrene-based derivatives are rare as a result of the limited number of controllable synthetic methods to prepare them. However, these materials are in great demand given their potential practical application in photics and biological imaging. Herein, we present a set of pyrene-based dipolar donor-π-acceptor (D-π-A) fluorophores with a wide-range of color tuning and large TPA cross-sections (up to 2200 GM at 780 nm) by regioselective substitution at the 1,3- and 6,8-positions under the perspective of theoretical analysis. The linear and nonlinear optical properties of these compounds have been studied. The near-identical emission wavelengths between the two-photon-excited fluorescence (TPEF) and one-photon excited fluorescence (OPEF) indicated that they are generated from the same fluorescent excited state by either one- or two-photon excitation. With the exception of the strong donor [N(CH3)2] appended fluorophore, the TPEF exhibited a large red-shift compared with the OPEF spectra as a result of the complicated working mechanisms in operation, including intramolecular charge transfer (ICT) and twisted intramolecular charge transfer (TICT). All fluorophores exhibit high two-photon cross-sections (or two-photon brightness, δΦ), especially for 1348 GM, which indicated that these materials can be used as colorants for probe and bioimaging applications.

AB - Two-photon absorption (TPA) properties of pyrene-based derivatives are rare as a result of the limited number of controllable synthetic methods to prepare them. However, these materials are in great demand given their potential practical application in photics and biological imaging. Herein, we present a set of pyrene-based dipolar donor-π-acceptor (D-π-A) fluorophores with a wide-range of color tuning and large TPA cross-sections (up to 2200 GM at 780 nm) by regioselective substitution at the 1,3- and 6,8-positions under the perspective of theoretical analysis. The linear and nonlinear optical properties of these compounds have been studied. The near-identical emission wavelengths between the two-photon-excited fluorescence (TPEF) and one-photon excited fluorescence (OPEF) indicated that they are generated from the same fluorescent excited state by either one- or two-photon excitation. With the exception of the strong donor [N(CH3)2] appended fluorophore, the TPEF exhibited a large red-shift compared with the OPEF spectra as a result of the complicated working mechanisms in operation, including intramolecular charge transfer (ICT) and twisted intramolecular charge transfer (TICT). All fluorophores exhibit high two-photon cross-sections (or two-photon brightness, δΦ), especially for 1348 GM, which indicated that these materials can be used as colorants for probe and bioimaging applications.

KW - charge transfer

KW - dipolar molecules

KW - donor–acceptor systems

KW - pyrene

KW - two-photon absorption

UR - http://www.scopus.com/inward/record.url?scp=85058065271&partnerID=8YFLogxK

U2 - 10.1002/cptc.201800053

DO - 10.1002/cptc.201800053

M3 - Article

AN - SCOPUS:85058065271

SN - 2367-0932

VL - 2

SP - 749

EP - 756

JO - ChemPhotoChem

JF - ChemPhotoChem

IS - 8

ER -

Two-Photon-Absorption Properties of Pyrene-Based Dipolar D-π-A Fluorophores

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this