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Title: Bisanthracene bis(dicarboxylic imide)s as soluble and stable NIR dyes
Authors: Yao, J.H. 
Chi, C. 
Wu, J. 
Loh, K.-P. 
Keywords: Anthracenes
Issue Date: 21-Sep-2009
Citation: Yao, J.H., Chi, C., Wu, J., Loh, K.-P. (2009-09-21). Bisanthracene bis(dicarboxylic imide)s as soluble and stable NIR dyes. Chemistry - A European Journal 15 (37) : 9299-9302. ScholarBank@NUS Repository.
Abstract: A series of soluble and stable near-infrared (NIR) dyes based on laterally expanded bisanthracene bis(dicarboxylic imide)s M1-M4, which can also be regarded as dibenzoperylene derivatives, was reported. The anthracene dicarboxylic imide dimer 5 was synthesized by [Ni(cod)2]-mediated Yamamoto homocoupling of 4b and this was followed by tBuOK- and 1,5- diazabicyclo[4.3.0]non-5-ene (DBN)-mediated cyclization reaction to afford the desired cis-bisanthracene bis(dicarboxylic imide)s M2 in 85% yield. The transisomer M3 was obtained in 8% yield by heating the anthracene dicarboxylic imide 4a in melted KOH. Separation of the compound 7a from other isomers was successful after the attachment of the 2,6-diisopropylaniline groups. The dimer 8 was then prepared by a similar Yamamoto coupling and followed by tBuOK- and DBN-mediated cyclization reaction. M1-M4 have very good solubility in common organic solvents such as CH2Cl2 and THF and they showed intense absorptions in NIR regions with absorption maximum at 830nm.
Source Title: Chemistry - A European Journal
ISSN: 09476539
DOI: 10.1002/chem.200901398
Appears in Collections:Staff Publications

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