AIE active triphenylamine-benzothiazole based motifs: ESIPT or ICT emission

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

doi:10.1039/c6ra02417c

AIE active triphenylamine-benzothiazole based motifs: ESIPT or ICT emission

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

IMRAM - Materials-Measurement Hybrid Research Center

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

35 Citations (Scopus)

Abstract

Two novel donor-π bridge-acceptor compounds containing excited state intramolecular proton transfer (ESIPT) and non-ESIPT units based on triphenylamine-benzothiazole were synthesized via Suzuki coupling reaction. Their photophysical properties were studied in the solid state as well as in solutions with solvents of different polarities. The fluorophores showed absorption in the UV region and emission in the visible region in both solutions and solid state. The optical properties of these compounds are highly dependent on solvent polarity. Significant positive solvatochromism (∼30 nm absorption and ∼80 nm emission red shift in polar solvents) were observed for both the compounds. Large Stokes shift (∼15000 cm^-1), polarity sensitive optical properties and very high quantum efficiencies (∼90%) in solvents and the solid state are the striking features of the synthesized compounds. Intramolecular charge transfer (ICT) characteristics of the compounds were supported experimentally and computationally. Halochromism and the intermolecular charge transfer phenomenon were used for investigation of ESIPT emission for compound 9 over ICT emission.

Original language	English
Pages (from-to)	26941-26949
Number of pages	9
Journal	RSC Advances
Volume	6
Issue number	32
DOIs	https://doi.org/10.1039/c6ra02417c
Publication status	Published - 2016

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title = "AIE active triphenylamine-benzothiazole based motifs: ESIPT or ICT emission",

abstract = "Two novel donor-π bridge-acceptor compounds containing excited state intramolecular proton transfer (ESIPT) and non-ESIPT units based on triphenylamine-benzothiazole were synthesized via Suzuki coupling reaction. Their photophysical properties were studied in the solid state as well as in solutions with solvents of different polarities. The fluorophores showed absorption in the UV region and emission in the visible region in both solutions and solid state. The optical properties of these compounds are highly dependent on solvent polarity. Significant positive solvatochromism (∼30 nm absorption and ∼80 nm emission red shift in polar solvents) were observed for both the compounds. Large Stokes shift (∼15000 cm-1), polarity sensitive optical properties and very high quantum efficiencies (∼90%) in solvents and the solid state are the striking features of the synthesized compounds. Intramolecular charge transfer (ICT) characteristics of the compounds were supported experimentally and computationally. Halochromism and the intermolecular charge transfer phenomenon were used for investigation of ESIPT emission for compound 9 over ICT emission.",

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

note = "Funding Information: V.S. P. and D. S. thank the JSPS Research Fellowship. This work was partly supported by a Grant-in-Aid for Scientific Research (No. 2604063, 26102011, 26810023, 26102001) from the Japan Society for the Promotion of Science (JSPS). Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6ra02417c",

language = "English",

volume = "6",

pages = "26941--26949",

journal = "RSC Advances",

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publisher = "Royal Society of Chemistry",

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T1 - AIE active triphenylamine-benzothiazole based motifs

T2 - ESIPT or ICT emission

AU - Padalkar, Vikas S.

AU - Sakamaki, Daisuke

AU - Kuwada, Kenji

AU - Tohnai, Norimitsu

AU - Akutagawa, Tomoyuki

AU - Sakai, Ken Ichi

AU - Seki, Shu

N1 - Funding Information: V.S. P. and D. S. thank the JSPS Research Fellowship. This work was partly supported by a Grant-in-Aid for Scientific Research (No. 2604063, 26102011, 26810023, 26102001) from the Japan Society for the Promotion of Science (JSPS). Publisher Copyright: © 2016 The Royal Society of Chemistry.

PY - 2016

Y1 - 2016

N2 - Two novel donor-π bridge-acceptor compounds containing excited state intramolecular proton transfer (ESIPT) and non-ESIPT units based on triphenylamine-benzothiazole were synthesized via Suzuki coupling reaction. Their photophysical properties were studied in the solid state as well as in solutions with solvents of different polarities. The fluorophores showed absorption in the UV region and emission in the visible region in both solutions and solid state. The optical properties of these compounds are highly dependent on solvent polarity. Significant positive solvatochromism (∼30 nm absorption and ∼80 nm emission red shift in polar solvents) were observed for both the compounds. Large Stokes shift (∼15000 cm-1), polarity sensitive optical properties and very high quantum efficiencies (∼90%) in solvents and the solid state are the striking features of the synthesized compounds. Intramolecular charge transfer (ICT) characteristics of the compounds were supported experimentally and computationally. Halochromism and the intermolecular charge transfer phenomenon were used for investigation of ESIPT emission for compound 9 over ICT emission.

AB - Two novel donor-π bridge-acceptor compounds containing excited state intramolecular proton transfer (ESIPT) and non-ESIPT units based on triphenylamine-benzothiazole were synthesized via Suzuki coupling reaction. Their photophysical properties were studied in the solid state as well as in solutions with solvents of different polarities. The fluorophores showed absorption in the UV region and emission in the visible region in both solutions and solid state. The optical properties of these compounds are highly dependent on solvent polarity. Significant positive solvatochromism (∼30 nm absorption and ∼80 nm emission red shift in polar solvents) were observed for both the compounds. Large Stokes shift (∼15000 cm-1), polarity sensitive optical properties and very high quantum efficiencies (∼90%) in solvents and the solid state are the striking features of the synthesized compounds. Intramolecular charge transfer (ICT) characteristics of the compounds were supported experimentally and computationally. Halochromism and the intermolecular charge transfer phenomenon were used for investigation of ESIPT emission for compound 9 over ICT emission.

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AIE active triphenylamine-benzothiazole based motifs: ESIPT or ICT emission

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