Multi-stimuli-responsive fluorescence switching from a novel organic polymorphic benzoimido-benzamide derivative

Jianai Chen; Xiaosong Guo; Yue Yu; Chunyu Liu; Weijun Li; Shitong Zhang; Jin Liu; Yujie Dong; Cheng Zhang; Wai Yeung Wong

doi:10.1016/j.jlumin.2021.118690

Multi-stimuli-responsive fluorescence switching from a novel organic polymorphic benzoimido-benzamide derivative

Jianai Chen, Xiaosong Guo, Yue Yu, Chunyu Liu, Weijun Li, Shitong Zhang, Jin Liu, Yujie Dong, Cheng Zhang, Wai Yeung Wong

Research output: Journal article publication › Journal article › Academic research › peer-review

9 Citations (Scopus)

Abstract

A novel organic polymorphic luminogen, (Z)-N-((benzoylimino) (4-(diphenylamino)phenyl)methyl)-N-(4-fluorophenyl)benzamide (DPA-PYZ-F), has been designed and synthesized successfully by a green photo-oxidation reaction. Two polymorphs (FB and FG) based on DPA-PYZ-F with different conformations display blue and green fluorescence, respectively. The emission of the newly obtained polymorphic molecule can be switched through the response to a mechanical force, thermal stimulus and protonic acid. The photophysical property tests and single crystal structural analysis disclosed that the mechanical force stimuli-responsive behavior of the FB and FG samples originate from the change of molecular arrangement. More significantly, FT-IR spectroscopy confirmed that the conformation transition from the FG to the FB could be achieved by thermal stimulus at 430 K. Additionally, protonation−deprotonation of the benzoylimino moieties in DPA-PYZ-F induced a remarkable fluorescence on-off characteristics upon protonic acid and thermal stimulus. The multi-stimuli response performance endows the new kind of molecule with the potential as a candidate for applications in mechanical force, thermal and protonic acid sensing.

Original language	English
Article number	118690
Journal	Journal of Luminescence
Volume	244
DOIs	https://doi.org/10.1016/j.jlumin.2021.118690
Publication status	Published - Apr 2022

Keywords

Mechanochromism
Multi-stimuli-responsive fluorescence
Polymorphs
Protonation effect

ASJC Scopus subject areas

Biophysics
Atomic and Molecular Physics, and Optics
General Chemistry
Biochemistry
Condensed Matter Physics

More information

10.1016/j.jlumin.2021.118690

Cite this

@article{ee21f36806e94ab6b5011ffd001c2738,

title = "Multi-stimuli-responsive fluorescence switching from a novel organic polymorphic benzoimido-benzamide derivative",

abstract = "A novel organic polymorphic luminogen, (Z)-N-((benzoylimino) (4-(diphenylamino)phenyl)methyl)-N-(4-fluorophenyl)benzamide (DPA-PYZ-F), has been designed and synthesized successfully by a green photo-oxidation reaction. Two polymorphs (FB and FG) based on DPA-PYZ-F with different conformations display blue and green fluorescence, respectively. The emission of the newly obtained polymorphic molecule can be switched through the response to a mechanical force, thermal stimulus and protonic acid. The photophysical property tests and single crystal structural analysis disclosed that the mechanical force stimuli-responsive behavior of the FB and FG samples originate from the change of molecular arrangement. More significantly, FT-IR spectroscopy confirmed that the conformation transition from the FG to the FB could be achieved by thermal stimulus at 430 K. Additionally, protonation−deprotonation of the benzoylimino moieties in DPA-PYZ-F induced a remarkable fluorescence on-off characteristics upon protonic acid and thermal stimulus. The multi-stimuli response performance endows the new kind of molecule with the potential as a candidate for applications in mechanical force, thermal and protonic acid sensing.",

keywords = "Mechanochromism, Multi-stimuli-responsive fluorescence, Polymorphs, Protonation effect",

author = "Jianai Chen and Xiaosong Guo and Yue Yu and Chunyu Liu and Weijun Li and Shitong Zhang and Jin Liu and Yujie Dong and Cheng Zhang and Wong, {Wai Yeung}",

note = "Funding Information: Thanks are due to the financial supports from National Natural Science Foundation of China ( 52073257 , 51673083 , 52103232 and 52073242 ) and Zhejiang Provincial Natural Science Foundation of China ( LY19E030006 , LQ19E030016 ). W.-Y. W. would also like to thank the Hong Kong Research Grants Council ( PolyU 153058/19 P ), Hong Kong Polytechnic University ( 1-ZE1C ) and The Endowed Professorship in Energy from Ms. Clarea Au (847 S) for the financial support. Publisher Copyright: {\textcopyright} 2021",

year = "2022",

month = apr,

doi = "10.1016/j.jlumin.2021.118690",

language = "English",

volume = "244",

journal = "Journal of Luminescence",

issn = "0022-2313",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - Multi-stimuli-responsive fluorescence switching from a novel organic polymorphic benzoimido-benzamide derivative

AU - Chen, Jianai

AU - Guo, Xiaosong

AU - Yu, Yue

AU - Liu, Chunyu

AU - Li, Weijun

AU - Zhang, Shitong

AU - Liu, Jin

AU - Dong, Yujie

AU - Zhang, Cheng

AU - Wong, Wai Yeung

N1 - Funding Information: Thanks are due to the financial supports from National Natural Science Foundation of China ( 52073257 , 51673083 , 52103232 and 52073242 ) and Zhejiang Provincial Natural Science Foundation of China ( LY19E030006 , LQ19E030016 ). W.-Y. W. would also like to thank the Hong Kong Research Grants Council ( PolyU 153058/19 P ), Hong Kong Polytechnic University ( 1-ZE1C ) and The Endowed Professorship in Energy from Ms. Clarea Au (847 S) for the financial support. Publisher Copyright: © 2021

PY - 2022/4

Y1 - 2022/4

N2 - A novel organic polymorphic luminogen, (Z)-N-((benzoylimino) (4-(diphenylamino)phenyl)methyl)-N-(4-fluorophenyl)benzamide (DPA-PYZ-F), has been designed and synthesized successfully by a green photo-oxidation reaction. Two polymorphs (FB and FG) based on DPA-PYZ-F with different conformations display blue and green fluorescence, respectively. The emission of the newly obtained polymorphic molecule can be switched through the response to a mechanical force, thermal stimulus and protonic acid. The photophysical property tests and single crystal structural analysis disclosed that the mechanical force stimuli-responsive behavior of the FB and FG samples originate from the change of molecular arrangement. More significantly, FT-IR spectroscopy confirmed that the conformation transition from the FG to the FB could be achieved by thermal stimulus at 430 K. Additionally, protonation−deprotonation of the benzoylimino moieties in DPA-PYZ-F induced a remarkable fluorescence on-off characteristics upon protonic acid and thermal stimulus. The multi-stimuli response performance endows the new kind of molecule with the potential as a candidate for applications in mechanical force, thermal and protonic acid sensing.

AB - A novel organic polymorphic luminogen, (Z)-N-((benzoylimino) (4-(diphenylamino)phenyl)methyl)-N-(4-fluorophenyl)benzamide (DPA-PYZ-F), has been designed and synthesized successfully by a green photo-oxidation reaction. Two polymorphs (FB and FG) based on DPA-PYZ-F with different conformations display blue and green fluorescence, respectively. The emission of the newly obtained polymorphic molecule can be switched through the response to a mechanical force, thermal stimulus and protonic acid. The photophysical property tests and single crystal structural analysis disclosed that the mechanical force stimuli-responsive behavior of the FB and FG samples originate from the change of molecular arrangement. More significantly, FT-IR spectroscopy confirmed that the conformation transition from the FG to the FB could be achieved by thermal stimulus at 430 K. Additionally, protonation−deprotonation of the benzoylimino moieties in DPA-PYZ-F induced a remarkable fluorescence on-off characteristics upon protonic acid and thermal stimulus. The multi-stimuli response performance endows the new kind of molecule with the potential as a candidate for applications in mechanical force, thermal and protonic acid sensing.

KW - Mechanochromism

KW - Multi-stimuli-responsive fluorescence

KW - Polymorphs

KW - Protonation effect

UR - http://www.scopus.com/inward/record.url?scp=85121811464&partnerID=8YFLogxK

U2 - 10.1016/j.jlumin.2021.118690

DO - 10.1016/j.jlumin.2021.118690

M3 - Journal article

AN - SCOPUS:85121811464

SN - 0022-2313

VL - 244

JO - Journal of Luminescence

JF - Journal of Luminescence

M1 - 118690

ER -

Multi-stimuli-responsive fluorescence switching from a novel organic polymorphic benzoimido-benzamide derivative

Abstract

Keywords

ASJC Scopus subject areas

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