ChemInform Abstract: DERIVATIVES OF NAPHTHALENE‐1,4,5,8‐TETRACARBOXYLIC ACID. II. CHROMATECITY OF BIS‐IMIDES OF SUBSTITUTED NAPHTHALENE‐1,4,5,8‐TETRACARBOXYLIC ACID

Bondarenko, E. F.; Shigalevskii, V. A.; Yugai, G. A.

doi:10.1002/chin.198228162

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“…Vollmann's synthesis 6a of core-substituted NDIs starts with naphthalene dianhydride 6 (Scheme ). The latter can be obtained in four steps from pyrene by subsequent chlorination, HCl elimination, and oxidation 6a. However, the procedure reported in this classical publication 6a could not be reproduced in a satisfying manner.…”

Section: Resultsmentioning

confidence: 98%

“…The dichlorosubstituted NDIs 7a , b are also not fluorescent. Upon introduction of amino substituents to the naphthalene core, significant changes in optical properties of NDIs were observed. ,,, Thus, one amino substituent (compounds 8a − c and 13a , 14a (Chart )) leads to red dyes with a new absorption band in the visible region at around 530 nm (Figure and Table ). For compounds bearing alkylamino groups ( 8a , c , 13a , 14a ) at the naphthalene core, the S 0 −S 1 band exhibits a shoulder at lower wavelengths.…”

Section: Resultsmentioning

confidence: 99%

“…NDIs with bathochromically shifted absorption maxima can be achieved by functionalization at the naphthalene core ) can even afford valuable fluorophores with fluorescence quantum yields up to 80% and tunable emission wavelengths from the green to red spectral region .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Optical and Redox Properties of Core-Substituted Naphthalene Diimide Dyes

2006

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2,6-Dichloronaphthalene dianhydride has been synthesized by a modified procedure. The imidization of this dichlorinated anhydride with amines and subsequent stepwise nucleophilic exchange of the chlorine atoms by alkyl- or arylamines afforded a series of hitherto unknown monoamino- and diamino-substituted naphthalene diimides. An alternative route for the synthesis of diamino-substituted naphthalene diimides is also reported. Optical and electrochemical properties of the newly synthesized amino-functionalized naphthalene diimides were studied in detail. The absorption maxima (530-620 nm) of these dyes are appreciably bathochromically shifted compared to those of the corresponding core-unsubstituted compounds. At the naphthalene core alkylamino-substituted diimides exhibit fluorescence quantum yields up to 60%.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%