fulltext23 - Red/Near-infrared BoronDipyrromethene Dyes as...

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Red/Near-infrared Boron–Dipyrromethene Dyes as Strongly Emitting Fluorophores A NA B. D ESCALZO , a H AI -J UN X U , b Z HEN S HEN , b AND K NUT R URACK a a Division I.5, Federal Institute for Materials Research and Testing (BAM), Berlin, Germany b State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, People’s Republic of China We present an overview of the state of the art in long-wavelength boron–dipyrromethene (BODIPY) Fuorophores, focusing on strategies to shift the absorption and emission bands into the red/near- infrared (NIR) range of the spectrum. This report also discusses chemical modi±cations of the chromophoric core to obtain analyte-responsive Fuorophores, including examples of pH and metal ion indicators. ²inally, we present a new series of phenanthrene-fused BODIPY dyes, emitting with high ef±ciency in the red/NIR region of the spectrum, as well as discussing potential applications thereof as probes. Key words: BODIPY dyes; near-infrared Fuorophores; Fuorescent indicators; charge transfer; ring fusion Introduction The search for new Fuorescent near-infrared (NIR) dyes has been promoted in the last few years mainly because of advancements in optical techniques for imaging, microarrays, electrophoresis, and the need for labels and optical sensors for biological and med- ical applications. 1 ±or such purposes, working in the red/NIR region of the spectrum is advantageous be- cause in the so-called biological window—between 650 and 900 nm—absorption of water, scattering of light, autoFuorescence, or absorption by tissues and cells is minimized. These facts, together with the development of potent and affordable excitation sources and detec- tors for the NIR, have fueled the design of new Fuo- rophores or Fuorescent materials that can be excited and that emit within the red visible or NIR region. Besides the wavelength of absorption, an ideal NIR dye should be bright, that is, should possess high mo- lar absorption coef²cients and Fuorescence quantum yields. Other important points to be considered in the development of new dyes are photostability and the possibility of further and facile functionalization for Address for correspondence: Ana B. Descalzo and Knut Rurack, Division I.5, ±ederal Institute for Materials Research and Testing (BAM), Richard-Willst¨atter-Str. 11, 12489 Berlin-Adlershof, Germany. ±ax: 49(30)-8104-5005. ana.descalzo@bam.de, knut.rurack@bam.de labeling purposes or the creation of Fuorescent indi- cators. In this respect, the design of long-wavelength boron–dipyrromethene (BODIPY) dyes has increas- ingly attracted attention in the last decade. 2 BODIPY dyes were ²rst described by Treibs and Kreuzer in 1968. 3 These compounds present typical features of cyanine dyes, such as high molar absorp- tion coef²cients, negligible dependence of the spectro- scopic properties on environmental polarity, narrow and structured absorption and emission bands, and small Stokes shifts. However, for classic cyanine dyes, such as Cy3 or Cy5, problems due to poor photo-
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This note was uploaded on 07/11/2010 for the course SPECTOGRAP 545 taught by Professor Gdf during the Spring '10 term at AIB College of Business.

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fulltext23 - Red/Near-infrared BoronDipyrromethene Dyes as...

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