Synthesis, Fluorescence Properties, and Head-to-Tail Regioselectivity in the Photodimerization of a Donor–Acceptor-Substituted Anthracene

Ihmels, Heiko

doi:10.1002/(sici)1099-0690(199907)1999:7<1595::aid-ejoc1595>3.0.co;2-d

Cited by 27 publications

(22 citation statements)

References 52 publications

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“…[16,32] Nevertheless, there are reports of regioselective head-to-tail dimerizations of other aza-heterocyclic aromatic compounds [33] and of a 2,6-donor ± acceptor-substituted anthracene. [34] The selectivity of the dimerization may be due to the thermal lability of the head-to-head isomers, since 1 H NMR spectroscopy indicated that very small amounts of head-to-head isomers are formed on photolysis, which then smoothly cyclorevert at room temperature. Since these dimers may be detected by NMR spectroscopy, they should be sufficiently long lived to permit their observation.…”

Section: Discussionmentioning

confidence: 99%

New Dyes Based on Amino-Substituted Acridizinium Salts-Synthesis and Exceptional Photochemical Properties

et al. 2000

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The novel amino-substituted acridizinium salts 5a and 5b represent a new class of cyanine dyes which exhibit intense color along with efficient fluorescence properties. These dyes show moderate solvatochromism in their absorption and emission spectra. The absorption and emission shifts of the two chromophores display a reasonable correlation with solvent parameters such as donor and acceptor number. It was found that the dyes 5a and 5b interact with DNA, with quenching of the band intensies accompanied with a red shift of the absorption and emission bands. Moreover, irradiation of salts 5a and 5b in the presence of DNA results in DNA damage. Solution photolysis of acridizinium salt 5a gave the head-to-tail dimers as the major products (>95%), whereas the acridizinium salt 5b afforded the anti-head-to-tail dimer along with both head-to-head isomers. The latter are thermally labile and rapidly revert to the monomer.

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Section: Discussionmentioning

confidence: 99%

New Dyes Based on Amino-Substituted Acridizinium Salts-Synthesis and Exceptional Photochemical Properties

et al. 2000

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“…But apart from functionalization at the meso positions (C9, C10) 78,85 the synthesis of such anthracene derivatives, especially with donor and acceptor functionalities in the lateral positions, is a rather elaborate project. [86][87][88][89][90] In contrast, the pyridinium unit within the benzo[b]quinolizinium already constitutes an intrinsic acceptor functionality, so that already the introduction of a single electron donating substituent in a "conjugated" position (i.e. position 2, 4, 6, 7, 9 or 11) establishes a donoracceptor system.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

Granzhan¹,

Ihmels²,

Tian³

2015

Arkivoc

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In this Account our efforts are described to establish the benzo[b]quinolizinium ion, also known as acridizinium or 4a-azoniaanthracene, as a water-soluble surrogate of anthracene for the development of selective fluorescent probes. It is demonstrated with selected examples that especially the 9-aminobenzo[b]quinolizinium is a donor-acceptor dye with favorable absorption and emission properties and may be used as a versatile building block for fluorescent light-up probes and ratiometric probes.

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“…Antracene and its derivatives are among the most useful polycyclic aromatic compounds [14]. In view of their fluorescent prperties, they are of practic1 interest as chemosensors and markers in supramolecular systems [1 1, 15-17].…”

Section: Fluorescent Chemosensorsmentioning

confidence: 99%

<title>Chemical recognition phase of the fluorescence chemical sensor for copper (II) ions in aqueous solution</title>

Kłonkowski

Ostaszewski²

2001

SPIE Proceedings

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We review the principles of optical sensors based on the use of the sol-gel technique, in particular their fabrication. We also report on potential applications of the recognition phases prepared by encapsulation of fluorescent chemosensors which have been designed by means of a supramolecular approach: two anthryl groups (the signalling subunit) linked to diaminodiethero group (the receptor subunit). Occurrence of the metal ionreceptor interaction is signalled through the enhancement of anthryl fluorescence. The enhancement takes place when the receptor is able to promote a photoinduced electron transfer mechanism. Cu(II) ions can be distinguished from other transition metal ions in aqueous solution by the recognition phase.

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Synthesis, Fluorescence Properties, and Head-to-Tail Regioselectivity in the Photodimerization of a Donor–Acceptor-Substituted Anthracene

Cited by 27 publications

References 52 publications

New Dyes Based on Amino-Substituted Acridizinium Salts-Synthesis and Exceptional Photochemical Properties

New Dyes Based on Amino-Substituted Acridizinium Salts-Synthesis and Exceptional Photochemical Properties

The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

<title>Chemical recognition phase of the fluorescence chemical sensor for copper (II) ions in aqueous solution</title>

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