Phenylethynyl-BODIPY Oligomers: Bright Dyes and Fluorescent Building Blocks

Cakmak, Yusuf
AKKAYA, Engin Umut
Boradiazaindacene dyes were converted Into phenylethynyl-BODIPY oligomers via a cycle of reactions, notably including Sonogashira couplings. As expected, as the number, n, of repeating units Increases, peak absorption and emission wavelengths are shifted to the red end of the visible spectrum, albeit with smaller increments as n Increases, Decyl groups help to keep the solubility remarkably high, and in addition to being very bright red-emitting fluorophores, their rigid rod-like structures could allow their use as functional building blocks.


Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde
Demir, Ayhan Sıtkı; Sesenoglu, O; Dunkelmann, P; Muller, M (American Chemical Society (ACS), 2003-06-12)
Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with methoxy and dimethoxy acetaldehyde and furnishes (R)-2-hydroxy-3-methoxy-1-arylpropan-1-one and (R)-2-hydroxy-3,3-dimethoxy-1-arylpropan-1-one in high yields and enantiomeric excess via acyloin linkage. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to carboligation.
Mechanistic Insights into the Reaction of N-Propargylated Pyrrole- and Indole-Carbaldehyde with Ammonia, Alkyl Amines, and Branched Amines: A Synthetic and Theoretical Investigation
Sari, Ozlem; Seybek, Ali Fatih; Kaya, Serap; Menges, Nurettin; ERDEM, SAFİYE; BALCI, METİN (Wiley, 2019-09-01)
The reaction of pyrrole- and indole-carbaldehydes having a propargyl group attached to the nitrogen atom with various amines was studied. The reaction with ammonia formed pyrrolo[1,2-a]pyrazine and pyrazino[1,2-a]indole while the reaction with alkylamines such as methyl, ethyl, hexyl, and benzylamines formed the corresponding pyrazinone derivatives. Unexpectedly, the reaction with allylamine and propargylamine formed pyrazine derivatives in which the allyl and propargyl groups were removed from the molecule...
Water-soluble green perylenediimide (PDI) dyes as potential sensitizers for photodynamic therapy
Yukruk, F; Dogan, AL; Canpinar, H; Guc, D; Akkaya, EU (American Chemical Society (ACS), 2005-07-07)
A series of water-soluble green perylenediimide (PDI) dyes have been synthesized. On red light excitation, these dyes were shown to be efficient generators of singlet oxygen, and in cell culture media, they were shown to display significant light-induced cytotoxic effects on the human erythroleukemia cell line (K-562). It appears that highly versatile PDI dyes are likely to find new applications in photodynamic therapy.
Organosilanols as Catalysts in Asymmetric Aryl Transfer Reactions
Özçubukçu, Salih; BOLM, Carsten (American Chemical Society (ACS), 2005-03-01)
Various ferrocene-based organosilanols have been synthesized in four steps starting from achiral ferrocene carboxylic acid. Applying these novel planar-chiral ferrocenes as catalysts in asymmetric phenyl transfer reactions to substituted benzaldehydes afforded products with high enantiomeric excesses. The best result (91% ee) was achieved in the addition to p-chlorobenzaldehyde with organosilanol 2b, which has a tert-butyl substituent on the oxazoline ring and an isopropyl group on the silanol fragment.
Photocatalytic hydrosilylation of conjugated dienes with triethylsilane in the presence of Cr(CO)(5)L(L=CO, P(CH3)(3), P(OCH3)(3))
Özkar, Saim; Kayran, C (Elsevier BV, 1997-04-15)
The effect of donor ligands on the chromium carbonyl photocatalysed hydrosilylation of 1,3-butadiene, 2-methyl-1,3-butadiene, 2,3-dimethyl-1,3-butadiene, trans-1,3-pentadiene with triethylsilane was studied. Photocatalytic hydrosilylation of dienes conducted in the presence of Cr(CO)(5)L (L = P(CH3)(3) or P(OCH3)(3)) yields the cis-1,4-adducts, 1-triethylsilyl-2-butene derivatives, as the main products; these have been isolated by distillation or preparative GC and fully characterised by NMR spectroscopy. A...
Citation Formats
Y. Cakmak and E. U. AKKAYA, “Phenylethynyl-BODIPY Oligomers: Bright Dyes and Fluorescent Building Blocks,” ORGANIC LETTERS, pp. 85–88, 2009, Accessed: 00, 2020. [Online]. Available: