Deactivation of the electronic excitation in the molecule of benzalalkylimine

Lyubarskaya, A. E.; Knyazhanskii, M. I.; Stryukov, M. B.

doi:10.1007/bf00610022

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2009

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“…3). Since simple benzalalkylimines are not fluorescent [18], the emissive properties of 4 and 5 are noteworthy and can most likely be assigned to the existence of this charge transfer excited state as well as the molecular rigidity arising from the chelate structure.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Properties of 2-(Dimesitylboryl)benzylideneamines

García‐Hernández

Gabbaı̈

2009

Zeitschrift Für Naturforschung B

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Lithiation of 2-(2-bromophenyl)-dioxolane (1) followed by reaction with dimesitylboron fluoride afforded 2-(2-dimesitylborylphenyl)-dioxolane (2) which was deprotected to afford 2-dimesitylboryl-benzaldehyde (3). Compound 3 reacts with aliphatic amines such as n-butylamine and ethanolamine to afford the corresponding imines 2-(dimesitylboryl)benzylidenebutylamine (4) and 2-(dimesitylboryl)benzylideneethanolamine (5), respectively. Structural studies indicate coordination of the imine-nitrogen atom to the boron center. Imines 4 and 5 emit a green fluorescence near 510 nm with quantum yields approaching 10 %. TD-DFT calculations suggest that this emission arises from an intramolecular charge-transfer excited state.

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Section: Resultsmentioning

confidence: 99%