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Synthesis and Structure‐Photophysics Evaluation of 2‐N‐Amino‐quinazolines: Small Molecule Fluorophores for Solution and Solid State

Abstract : 2-N-aminoquinazolines were prepared through consecutive SNAr functionalization. X-ray structures display the nitrogen lone pair of the 2-N-morphilino group in conjugation with the electron deficient quinazoline core and thus representing electronic push-pull systems. 2-N-aminoquinazolines show a positive solvatochromism and are fluorescent in solution and in solid state with quantum yields up to 0.73. Increase in electron donor strength of the 2-amino substituent causes a red-shift of the intramolecular charge transfer (ICT) band (300-400 nm); whereas the photoluminescence emission maxima (350-450 nm) is also red-shifted significantly along with an enhancement in photoluminescence efficiency. HOMO-LUMO energies were estimated by a combination of electrochemical and photophysical methods and correlate well to those obtained by computational methods. ICT properties are theoretically attributed to an excitation to Rydberg-MO in SAC-CI method, which can be interpreted as n-pi* excitation. 7-Amino-2-N-morpholino-4-methoxyquinazoline responds to acidic conditions with significant increases in photoluminescence intensity revealing a new turn-on/off fluorescence probe.
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Submitted on : Friday, November 18, 2022 - 9:25:35 AM
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Miho Motoyama, Thu‐hong Doan, Paulina Hibner‐kulicka, Ryo Otake, Malgorzata Lukarska, et al.. Synthesis and Structure‐Photophysics Evaluation of 2‐N‐Amino‐quinazolines: Small Molecule Fluorophores for Solution and Solid State. Chemistry - An Asian Journal, 2021, 16 (15), pp.2087-2099. ⟨10.1002/asia.202100534⟩. ⟨hal-03361225⟩

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