ChemInform Abstract: DERIVATIZATION OF AMINES WITH 4‐SUBSTITUTED 7‐NITRO‐2,1,3‐BENZOXADIAZOLES

Heberer, H.; Kersting, Hans Josef; Matschiner, H.

doi:10.1002/chin.198539215

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“…Following the general procedure described in the literature , 4‐chloro‐7‐nitrobenzofuran (Sigma‐Aldrich, 100 mg, 501.1 μ mol) was stirred in 6 ml of HPLC grade methanol at 0°C under an argon atmosphere. After 30 min, hexylamine (Sigma‐Aldrich, 0.08 ml, 61.28 mg, 605.6 μ mol) was added dropwise, upon which the solution changed color from bright yellow to light red.…”

Section: Methodsmentioning

confidence: 99%

Unveiling the Triplet State of a 4‐Amino‐7‐Nitrobenzofurazan Derivative in Cyclohexane

Sveen

Macia

Zaremberg

et al. 2015

Photochem & Photobiology

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The nitrobenzofurazan (NBD) moiety has gained tremendous popularity over the last decades due to its fluorogenic nature. Indeed, upon interaction with aliphatic amines, it generates a stable fluorescent adduct, which has been used for protein and lipid labeling. In fact the 4-amino substituted NBD belongs to the broad family of intramolecular charge transfer molecules, with the amino group acting as an electron donor upon photoexcitation, and the nitro group as an electron acceptor. Although the singlet excited state of 4-amino NBD derivatives has been abundantly studied, investigation of its triplet manifold is scarce and even the absence of intersystem crossing for this type of molecules has been suggested. However, intramolecular charge transfer molecules are known to undergo intersystem crossing and high phosphorescence quantum yields have been reported in a nonpolar solvent. In the present paper, we have investigated the photophysical and photochemical properties of N-hexyl-7-nitrobenzo[c][1,2,5]xadiazole-4-amine. We have shown the existence of a triplet state for this molecule in cyclohexane via nanosecond laser flash photolysis. Interestingly, deactivation of the triplet state leads to photoproducts formation, which are only present in the absence of oxygen.

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Section: Methodsmentioning

confidence: 99%

Unveiling the Triplet State of a 4‐Amino‐7‐Nitrobenzofurazan Derivative in Cyclohexane

Sveen

Macia

Zaremberg

et al. 2015

Photochem & Photobiology

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ChemInform Abstract: DERIVATIZATION OF AMINES WITH 4‐SUBSTITUTED 7‐NITRO‐2,1,3‐BENZOXADIAZOLES

Abstract: Die Titelverbindungen (I), (IV) bzw. (VII) werden durch Umsetzen mit den Aminen (II), (V) bzw. (VIII) unter variierenden Synthesebedingungen in die 28 neuen 4‐Aminoderivate (III), (VI) und (IX) übergeführt.

Cited by 1 publication

References 1 publication

Unveiling the Triplet State of a 4‐Amino‐7‐Nitrobenzofurazan Derivative in Cyclohexane

Unveiling the Triplet State of a 4‐Amino‐7‐Nitrobenzofurazan Derivative in Cyclohexane

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