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Full color emissions based on intramolecular charge transfer effect modulated by formyl and boron-dipyrromethene moieties
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1763-9383
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2017 (English)In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 136, 480-487 p.Article in journal (Refereed) Published
Abstract [en]

From the simple one-pot Vilsmeier formylation of 9-diphenylaminoanthracence, mono-, di- and tri-formyl products were successfully synthesized and the yields for the individual products can be optimized by varying the equivalents of the Vilsmeier reagent and changing the reaction temperature. The four obtained aldehydes exhibit distinct optical properties, with the emission maxima varying in a large wavelength range of 455–593 nm, despite their similar structures. The intramolecular charge transfer effect can be effectively modulated by varying the numbers and positions of the formyl groups, resulting in the observed distinct optical properties. Based on the aldehydes, the corresponding boron-dipyrromethenes were also synthesized. Similarly, the intramolecular charge transfer effect and the optical properties can be effectively modulated by the numbers and positions of the boron-dipyrromethene moieties. To further modulate the intramolecular charge transfer effect and red shift the emission, the dimethoxy-substituted 9-diphenylaminoanthracence was also used for synthesizing the corresponding aldehyde and boron-dipyrromethene. Thus, full color emissions within the wavelength range of 455–704 nm were successfully achieved based on modulating the intramolecular charge transfer. © 2016 Elsevier Ltd

Place, publisher, year, edition, pages
2017. Vol. 136, 480-487 p.
Keyword [en]
Boron-dipyrromethenes, Full color emission, Intramolecular charge transfer, Aldehydes, Boron, Chemical reactions, Color, Dies, Optical properties, Boron dipyrromethene, Boron dipyrromethenes, Full color, Intra-molecular charge transfer, Large wavelength range, Reaction temperature, Vilsmeier reagent, Wavelength ranges, Charge transfer
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Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-195125DOI: 10.1016/j.dyepig.2016.08.069ISI: 000387837200057ScopusID: 2-s2.0-84986332735OAI: oai:DiVA.org:kth-195125DiVA: diva2:1048259
Note

Funding Details: 91227201, NSFC, National Natural Science Foundation of China, QC 20161121

Available from: 2016-11-21 Created: 2016-11-02 Last updated: 2016-12-13Bibliographically approved

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