π–π Interactions: Influence on Molecular Packing and Solid-State Emission of ESIPT and non-ESIPT Motifs

Vikas S. Padalkar; Daisuke Sakamaki; Kenji Kuwada; Akifumi Horio; Haruka Okamoto; Norimitsu Tohnai; Tomoyuki Akutagawa; Ken Ichi Sakai; Shu Seki

doi:10.1002/ajoc.201600159

π–π Interactions: Influence on Molecular Packing and Solid-State Emission of ESIPT and non-ESIPT Motifs

Vikas S. Padalkar, Daisuke Sakamaki, Kenji Kuwada, Akifumi Horio, Haruka Okamoto, Norimitsu Tohnai, Tomoyuki Akutagawa, Ken Ichi Sakai, Shu Seki

IMRAM - Materials-Measurement Hybrid Research Center

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

30 Citations (Scopus)

Abstract

Novel, triphenylamino benzothiazole-based excited-state intramolecular proton transfer (ESIPT) and non-ESIPT fluorophores were prepared by Suzuki coupling reactions. Their photophysical properties in solution, aqueous suspension, and in the solid state were systematically investigated. High fluorescence quantum efficiencies (Φ_sol≈95 %; Φ_solid≈88 %), moderate Stokes shifts (≈8000 cm⁻¹), microenvironment-sensitive and molecular-framework-dependent emission are the striking features of the protocol described here. Solid-state emission was modulated and interpreted as a crossover effect of π–π interactions using single-crystal X-ray analyses. The nonplanar/twisted framework of the system helps to avoid noncovalent interactions, facilitating the suppression of fluorescence quenching in the solid state with high quantum efficiency over 88 %.

Original language	English
Pages (from-to)	938-945
Number of pages	8
Journal	Asian Journal of Organic Chemistry
Volume	5
Issue number	7
DOIs	https://doi.org/10.1002/ajoc.201600159
Publication status	Published - 2016 Jul 1

Keywords

aggregation-induced emission
excited-state intramolecular proton transfer
fluorescence
molecular packing
photophysics

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title = "π–π Interactions: Influence on Molecular Packing and Solid-State Emission of ESIPT and non-ESIPT Motifs",

abstract = "Novel, triphenylamino benzothiazole-based excited-state intramolecular proton transfer (ESIPT) and non-ESIPT fluorophores were prepared by Suzuki coupling reactions. Their photophysical properties in solution, aqueous suspension, and in the solid state were systematically investigated. High fluorescence quantum efficiencies (Φsol≈95 %; Φsolid≈88 %), moderate Stokes shifts (≈8000 cm−1), microenvironment-sensitive and molecular-framework-dependent emission are the striking features of the protocol described here. Solid-state emission was modulated and interpreted as a crossover effect of π–π interactions using single-crystal X-ray analyses. The nonplanar/twisted framework of the system helps to avoid noncovalent interactions, facilitating the suppression of fluorescence quenching in the solid state with high quantum efficiency over 88 %.",

keywords = "aggregation-induced emission, excited-state intramolecular proton transfer, fluorescence, molecular packing, photophysics",

author = "Padalkar, {Vikas S.} and Daisuke Sakamaki and Kenji Kuwada and Akifumi Horio and Haruka Okamoto and Norimitsu Tohnai and Tomoyuki Akutagawa and Sakai, {Ken Ichi} and Shu Seki",

note = "Funding Information: This study was funded, in part, by the Government of Guam, Department of Agriculture, Division of Wildlife Resources Project No. F-1R-4 (2440), Freshwater Monitoring under the Sport Fish Restoration Program. This is contribution number 422 from the University of Guam Marine Laboratory. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = jul,

day = "1",

doi = "10.1002/ajoc.201600159",

language = "English",

volume = "5",

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journal = "Asian Journal of Organic Chemistry",

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TY - JOUR

T1 - π–π Interactions

T2 - Influence on Molecular Packing and Solid-State Emission of ESIPT and non-ESIPT Motifs

AU - Padalkar, Vikas S.

AU - Sakamaki, Daisuke

AU - Kuwada, Kenji

AU - Horio, Akifumi

AU - Okamoto, Haruka

AU - Tohnai, Norimitsu

AU - Akutagawa, Tomoyuki

AU - Sakai, Ken Ichi

AU - Seki, Shu

N1 - Funding Information: This study was funded, in part, by the Government of Guam, Department of Agriculture, Division of Wildlife Resources Project No. F-1R-4 (2440), Freshwater Monitoring under the Sport Fish Restoration Program. This is contribution number 422 from the University of Guam Marine Laboratory. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2016/7/1

Y1 - 2016/7/1

N2 - Novel, triphenylamino benzothiazole-based excited-state intramolecular proton transfer (ESIPT) and non-ESIPT fluorophores were prepared by Suzuki coupling reactions. Their photophysical properties in solution, aqueous suspension, and in the solid state were systematically investigated. High fluorescence quantum efficiencies (Φsol≈95 %; Φsolid≈88 %), moderate Stokes shifts (≈8000 cm−1), microenvironment-sensitive and molecular-framework-dependent emission are the striking features of the protocol described here. Solid-state emission was modulated and interpreted as a crossover effect of π–π interactions using single-crystal X-ray analyses. The nonplanar/twisted framework of the system helps to avoid noncovalent interactions, facilitating the suppression of fluorescence quenching in the solid state with high quantum efficiency over 88 %.

AB - Novel, triphenylamino benzothiazole-based excited-state intramolecular proton transfer (ESIPT) and non-ESIPT fluorophores were prepared by Suzuki coupling reactions. Their photophysical properties in solution, aqueous suspension, and in the solid state were systematically investigated. High fluorescence quantum efficiencies (Φsol≈95 %; Φsolid≈88 %), moderate Stokes shifts (≈8000 cm−1), microenvironment-sensitive and molecular-framework-dependent emission are the striking features of the protocol described here. Solid-state emission was modulated and interpreted as a crossover effect of π–π interactions using single-crystal X-ray analyses. The nonplanar/twisted framework of the system helps to avoid noncovalent interactions, facilitating the suppression of fluorescence quenching in the solid state with high quantum efficiency over 88 %.

KW - aggregation-induced emission

KW - excited-state intramolecular proton transfer

KW - fluorescence

KW - molecular packing

KW - photophysics

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π–π Interactions: Influence on Molecular Packing and Solid-State Emission of ESIPT and non-ESIPT Motifs

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