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RISS 인기검색어
- 검색키워드
- 저자 : Koszarna, Beata (검색결과 2 건)
- 무료
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Purc, Anna,Koszarna, Beata,Iachina, Irina,Friese, Daniel H.,Tasior, Mariusz,Sobczyk, Krzysztof,Pę,dziń,ski, Tomasz,Brewer, Jonathan,Gryko, Daniel T. Royal Society of Chemistry 2017 ORGANIC CHEMISTRY FRONTIERS Vol.4 No.5
<▼1><P>Benzofuran has been proven to be the versatile substituent for tuning the optics of diketopyrrolopyrroles.</P></▼1><▼2><P>An in-depth investigation of the reaction of substituted salicylaldehydes with chloroacetonitrile led to the development of new conditions for the synthesis of 2-cyanobenzofurans. The crucial improvement lies in the use of phase-transfer catalysis in the second step, <I>i.e.</I>, intramolecular aldol type condensation. In a two-step process, the reactants were transformed into a library of 3,6-bis(benzofuran-2-yl)diketopyrrolopyrroles. We show that the presence of a methyl group in a position adjacent to the cyano functionality only slightly decreased the yield of diketopyrrolopyrroles (to 30–57%). An analysis of the relationship between the degree of polarization/planarization of aryl-diketopyrrolopyrroles and their one- and two-photon spectroscopic properties is reported. Careful design of the desired dyes and enhanced control of their ability to assume a planar molecular structure resulted in interesting photophysical properties, such as absorption and emission in the so-called biological window. Despite having less promising linear spectroscopic properties, the deplanarized molecules possess pretty strong two-photon absorbing properties. Placing methyl groups at adjacent positions to the linkage between benzofuran and the DPP core caused the formation of yellow-emitting dyes with almost quantitative fluorescence quantum yield, moderate Stokes shift and reasonable two-photon absorption cross-sections.</P></▼2>
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Synthesis of <i>trans</i>-A<sub>2</sub>B<sub>2</sub>-Porphyrins Bearing Phenylethynyl Substituents
Nowak-Kró,l, Agnieszka,Koszarna, Beata,Yoo, Su Yeon,Chromiń,ski, Jan,Wȩ,cławski, Marek K.,Lee, Chang-Hee,Gryko, Daniel T. American Chemical Society 2011 Journal of organic chemistry Vol.76 No.8
<P>Efficient and convenient conditions for the preparation of <I>trans</I>-A<SUB>2</SUB>B<SUB>2</SUB>-porphyrins bearing two phenylethynyl moieties directly from phenylpropargyl aldehydes and dipyrromethanes of diversified lipophilicity and reactivity have been developed. This new procedure allows the preparation of a library of porphyrins of this architecture with a wide range of substituents. Thanks to the identification of the reagent solubility as one of the key factors influencing the yield of the porphyrinogens, we were able to improve yields to ca. 30%. The scope and limitations of two sets of conditions have been explored. The methodological advantage of this approach is its straightforward access to building blocks and the formation of the porphyrin core in the last step without the need for deprotection of the triple bond or bromination and consecutive coupling reaction, which often demands copper salts to proceed smoothly, especially with electron-deficient alkyne partners. Therefore, it prevents undesired copper porphyrin formation, as well as the need for utilizing expensive alkynes. A two-step method for the preparation of phenylpropargyl aldehydes has also been refined.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2011/joceah.2011.76.issue-8/jo1025578/production/images/medium/jo-2010-025578_0007.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jo1025578'>ACS Electronic Supporting Info</A></P>
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