Design and synthesis of light-harvesting rotor based on 1,8-naphthalimide units

Nikolai I. Georgiev; Nevena V. Marinova; Vladimir B. Bojinov

doi:10.1016/j.jphotochem.2020.112733

Design and synthesis of light-harvesting rotor based on 1,8-naphthalimide units

Nikolai I. Georgiev
, Nevena V. Marinova
, Vladimir B. Bojinov^*

^*Corresponding author for this work

University of Chemical Technology and Metallurgy Sofia

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

19 Citations (Scopus)

Abstract

A novel pH and viscosity fluorescence sensing multicomponent molecular device based on 1,8-naphthalimide fluorophores is synthesized and investigated. The system is designed as a light-harvesting antenna where energy supplier, molecular rotor and molecular “on-off” switcher are integrated. The peripheral 1,8-naphthalimide energy suppliers transfer rapidly the trapped energy to the core molecular rotor through high efficient FRET (99 %). The 4-piperazinyl-1,8-naphthalimide core excitation results in a TICT driven molecular motion. Due to the non-emissive de-excitation nature of the TICT core fluorophore, system shows low yellow-green fluorescence that is a “power-on”/“rotor-on” state. The protonation of the methylpiperazine amine destabilized TICT process thus indicating a “power-on”/“rotor-off” system state.

Original language	English
Article number	112733
Journal	Journal of Photochemistry and Photobiology A: Chemistry
Volume	401
DOIs	https://doi.org/10.1016/j.jphotochem.2020.112733
Publication status	Published - 1 Oct 2020
Externally published	Yes

Keywords

1,8-Naphthalimide
Energy transfer
Fluorescent pH sensor
Light-harvesting rotor
Twisted internal charge transfer (TICT)
Viscosity sensing

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10.1016/j.jphotochem.2020.112733

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@article{a05245d5e8f44e13a5e37c91970453e7,

title = "Design and synthesis of light-harvesting rotor based on 1,8-naphthalimide units",

abstract = "A novel pH and viscosity fluorescence sensing multicomponent molecular device based on 1,8-naphthalimide fluorophores is synthesized and investigated. The system is designed as a light-harvesting antenna where energy supplier, molecular rotor and molecular “on-off” switcher are integrated. The peripheral 1,8-naphthalimide energy suppliers transfer rapidly the trapped energy to the core molecular rotor through high efficient FRET (99 \%). The 4-piperazinyl-1,8-naphthalimide core excitation results in a TICT driven molecular motion. Due to the non-emissive de-excitation nature of the TICT core fluorophore, system shows low yellow-green fluorescence that is a “power-on”/“rotor-on” state. The protonation of the methylpiperazine amine destabilized TICT process thus indicating a “power-on”/“rotor-off” system state.",

keywords = "1,8-Naphthalimide, Energy transfer, Fluorescent pH sensor, Light-harvesting rotor, Twisted internal charge transfer (TICT), Viscosity sensing",

author = "Georgiev, \{Nikolai I.\} and Marinova, \{Nevena V.\} and Bojinov, \{Vladimir B.\}",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier B.V.",

year = "2020",

month = oct,

day = "1",

doi = "10.1016/j.jphotochem.2020.112733",

language = "English",

volume = "401",

journal = "Journal of Photochemistry and Photobiology A: Chemistry",

issn = "1010-6030",

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TY - JOUR

T1 - Design and synthesis of light-harvesting rotor based on 1,8-naphthalimide units

AU - Georgiev, Nikolai I.

AU - Marinova, Nevena V.

AU - Bojinov, Vladimir B.

PY - 2020/10/1

Y1 - 2020/10/1

N2 - A novel pH and viscosity fluorescence sensing multicomponent molecular device based on 1,8-naphthalimide fluorophores is synthesized and investigated. The system is designed as a light-harvesting antenna where energy supplier, molecular rotor and molecular “on-off” switcher are integrated. The peripheral 1,8-naphthalimide energy suppliers transfer rapidly the trapped energy to the core molecular rotor through high efficient FRET (99 %). The 4-piperazinyl-1,8-naphthalimide core excitation results in a TICT driven molecular motion. Due to the non-emissive de-excitation nature of the TICT core fluorophore, system shows low yellow-green fluorescence that is a “power-on”/“rotor-on” state. The protonation of the methylpiperazine amine destabilized TICT process thus indicating a “power-on”/“rotor-off” system state.

AB - A novel pH and viscosity fluorescence sensing multicomponent molecular device based on 1,8-naphthalimide fluorophores is synthesized and investigated. The system is designed as a light-harvesting antenna where energy supplier, molecular rotor and molecular “on-off” switcher are integrated. The peripheral 1,8-naphthalimide energy suppliers transfer rapidly the trapped energy to the core molecular rotor through high efficient FRET (99 %). The 4-piperazinyl-1,8-naphthalimide core excitation results in a TICT driven molecular motion. Due to the non-emissive de-excitation nature of the TICT core fluorophore, system shows low yellow-green fluorescence that is a “power-on”/“rotor-on” state. The protonation of the methylpiperazine amine destabilized TICT process thus indicating a “power-on”/“rotor-off” system state.

KW - 1,8-Naphthalimide

KW - Energy transfer

KW - Fluorescent pH sensor

KW - Light-harvesting rotor

KW - Twisted internal charge transfer (TICT)

KW - Viscosity sensing

UR - https://www.scopus.com/pages/publications/85087392317

U2 - 10.1016/j.jphotochem.2020.112733

DO - 10.1016/j.jphotochem.2020.112733

M3 - Article

AN - SCOPUS:85087392317

SN - 1010-6030

VL - 401

JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

M1 - 112733

ER -

Design and synthesis of light-harvesting rotor based on 1,8-naphthalimide units

Abstract

Keywords

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