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Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

Masayori Hagimori, Tatsusada Yoshida, Yasuhisa Nishimura, Yukiko Ogawa and Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587. https://doi.org/10.3762/bjoc.18.60

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Supporting Information File 1: General information, synthesis of 3a,b, and 4a–e, experimental procedure of fluorescence, theoretical computation method measurements, NMR, UV–vis, and fluorescence spectra.
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Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

Masayori Hagimori, Tatsusada Yoshida, Yasuhisa Nishimura, Yukiko Ogawa and Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587. https://doi.org/10.3762/bjoc.18.60

How to Cite

Hagimori, M.; Yoshida, T.; Nishimura, Y.; Ogawa, Y.; Tanaka, K. Beilstein J. Org. Chem. 2022, 18, 580–587. doi:10.3762/bjoc.18.60

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TY  - JOUR
A1  - Hagimori, Masayori
A1  - Yoshida, Tatsusada
A1  - Nishimura, Yasuhisa
A1  - Ogawa, Yukiko
A1  - Tanaka, Keitaro
T1  - Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties
JF  - Beilstein Journal of Organic Chemistry
PY  - 2022///
VL  - 18
SP  - 580
EP  - 587
SN  - 1860-5397
DO  - 10.3762/bjoc.18.60
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.18.60
KW  - acceptor–donor–acceptor
KW  - AIEE
KW  - low molecular weight
KW  - one-pot reaction
KW  - ((pyridin-2-yl)amino)maleimide
KW  - TD-DFT calculation
N2  - Novel pyridine-based fluorescing compounds, viz. pyrido[1,2-a]pyrrolo[3,4-d]pyrimidines 3a,b and N-methyl-4-((pyridin-2-yl)amino)maleimides 4a–e, were selectively prepared by a one-pot reaction between a functionalized maleimide and 2-aminopyridines with electron-donating or electron-withdrawing groups at position 5 and were investigated photophysically and computationally. The photophysical studies revealed that all the synthesized compounds exhibited fluorescence in organic solvents, while N-methyl-4-((pyridin-2-yl)amino)-substituted maleimide derivatives 4a–e, which are based on an acceptor–donor–acceptor (A–D–A) system, exhibited aggregation-induced emission enhancement (AIEE) properties in aqueous media. Compounds 4a and 4e, bearing electron-withdrawing groups (Br and CF3, respectively) showed 7.0 and 15 times fluorescence enhancement. Time-dependent density functional theory (TD-DFT) calculations were performed to gain better insight into the electronic nature of the compounds with and without AIEE properties.
ER  -

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Scholarly Works

Hagimori, M.; Yoshida, T.; Tsutsumi, T.; Hara, F.; Takada, S.; Ogawa, Y.; Tanaka, K. Aggregation-Induced Luminescent 3-Phenylpyrano[4,3-b]quinolizine Derivatives as Photosensitizers with Anti-Cancer Properties. Molecules (Basel, Switzerland) 2025, 30, 1422. doi:10.3390/molecules30071422

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