Synthesis of ester-substituted dihydroacridine derivatives and their spectroscopic properties

Ryota Suzuki, Reiki Tada, Takumi Hosoda, Youhei Miura, Naoki Yoshioka

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Three dihydroacridine derivatives, 2,7-bis(4-methoxycarbonylphenyl)-9,9-diphenyl-9,10-dihydroacridine (1), 2,8-bis(4-methoxycarbonylphenyl)-10,10-diphenyl-5,10-dihydrophenazasiline (2), and 2,7,9,9-tetraphenyl-9,10-dihydroacridine (3), were prepared and their spectroscopic properties were investigated. These compounds exhibited relatively high quantum yields in a range of solvents. The emission spectra of 1 and 2 displayed large solvatochromic shifts, while the fluorescence solvatochromic behavior was not observed in 3. The intramolecular charge transfer (CT) process from the electron donating moiety at the NH site to the electron withdrawing ester moiety occurs in the excited states of 1 and 2. The increase in the dipole moment induced by the CT process was determined to cause the positive fluorescence solvatochromism. The differences between the excited and ground state dipole moments based on the Lippert-Mataga expression were estimated. The effect of the push-pull substitution in the dihydroacridine π-conjugated system was also discussed using a computational method.

Original languageEnglish
Pages (from-to)2920-2926
Number of pages7
JournalNew Journal of Chemistry
Volume40
Issue number3
DOIs
Publication statusPublished - 2016

Fingerprint

Dipole moment
Excited states
Charge transfer
Esters
Fluorescence
Derivatives
Electrons
Quantum yield
Computational methods
Ground state
Substitution reactions
diphenyl
acridan

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Materials Chemistry

Cite this

Synthesis of ester-substituted dihydroacridine derivatives and their spectroscopic properties. / Suzuki, Ryota; Tada, Reiki; Hosoda, Takumi; Miura, Youhei; Yoshioka, Naoki.

In: New Journal of Chemistry, Vol. 40, No. 3, 2016, p. 2920-2926.

Research output: Contribution to journalArticle

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abstract = "Three dihydroacridine derivatives, 2,7-bis(4-methoxycarbonylphenyl)-9,9-diphenyl-9,10-dihydroacridine (1), 2,8-bis(4-methoxycarbonylphenyl)-10,10-diphenyl-5,10-dihydrophenazasiline (2), and 2,7,9,9-tetraphenyl-9,10-dihydroacridine (3), were prepared and their spectroscopic properties were investigated. These compounds exhibited relatively high quantum yields in a range of solvents. The emission spectra of 1 and 2 displayed large solvatochromic shifts, while the fluorescence solvatochromic behavior was not observed in 3. The intramolecular charge transfer (CT) process from the electron donating moiety at the NH site to the electron withdrawing ester moiety occurs in the excited states of 1 and 2. The increase in the dipole moment induced by the CT process was determined to cause the positive fluorescence solvatochromism. The differences between the excited and ground state dipole moments based on the Lippert-Mataga expression were estimated. The effect of the push-pull substitution in the dihydroacridine π-conjugated system was also discussed using a computational method.",
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AU - Hosoda, Takumi

AU - Miura, Youhei

AU - Yoshioka, Naoki

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AB - Three dihydroacridine derivatives, 2,7-bis(4-methoxycarbonylphenyl)-9,9-diphenyl-9,10-dihydroacridine (1), 2,8-bis(4-methoxycarbonylphenyl)-10,10-diphenyl-5,10-dihydrophenazasiline (2), and 2,7,9,9-tetraphenyl-9,10-dihydroacridine (3), were prepared and their spectroscopic properties were investigated. These compounds exhibited relatively high quantum yields in a range of solvents. The emission spectra of 1 and 2 displayed large solvatochromic shifts, while the fluorescence solvatochromic behavior was not observed in 3. The intramolecular charge transfer (CT) process from the electron donating moiety at the NH site to the electron withdrawing ester moiety occurs in the excited states of 1 and 2. The increase in the dipole moment induced by the CT process was determined to cause the positive fluorescence solvatochromism. The differences between the excited and ground state dipole moments based on the Lippert-Mataga expression were estimated. The effect of the push-pull substitution in the dihydroacridine π-conjugated system was also discussed using a computational method.

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