4.4- Difluoro-4-bora-3a,4a-diaza-s-indacene BODIPY

The optical properties of organic dyes (Fig. ld-f, Table 1) are controlled by the nature of the electronic transition(s) involved [4], The emission occurs either from an electronic state delocalized over the whole chromophore (the corresponding fluorophores are termed here as resonant or mesomeric dyes) or from a charge transfer (CT) state formed via intramolecular charge transfer (ICT) from the initially excited electronic state (the corresponding fluorophores are referred to as CT dyes) [4], Bioanalytically relevant fluorophores like fluoresceins, rhodamines, most 4,4 -difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPY dyes), and cyanines (symmetric... 

BODIPY, 4,4-difluoro-4-bora-3a.4a-diaza-s-indacene. BODIPY is a trademark of Molecular Probes, Inc. 

Previously reported selective potent GABAc antagonists (S)- and (/ )-4-ACPBPA were used for the design of the fluorescent GABAc antagonists. To introduce molecular flexibility into the conjugated fluorescent ligand, Hanrahan et al. chose a linker size that varied from zero to ten carbon atoms and three different fluorophores [NMA (AT-methylanthranilic acid), 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) and 7-nitrobenz-2-oxa-l,3-diazol-4-yl chloride... 

The system was quite efficient and was probably an inspiration for Jong Hwa Jung et al. [143] who, more recently, have proposed a similarly engineered system for the sensing and separation of toxic species like lead and mercury in different matrices. They have synthesized nickel nanoparticles coated with a silica shell (30 0 nm in diameter), then grafted with a di-silanized 4,4-difluoro-4-bora-3a,-4a-diaza-s-indacene (BODIPY) derivative (Fig. 29). This dye, buffered at pH 7, is... 

Chen, J., A. Burghart, A. Derecskei-Kovacs, and K. Burges. 2000. 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes modified for extended conjugation and restricted bond rotations. J Org Chem 65 (10) 2900-2906. 

Fluorophores containing 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene as a core skeleton are commonly designated as BODIPY fluorophores. Due to their useful photophysical properties including high fluorescence quantum yields, high molar absorption coefficient, narrow absorption and emission band width, and their high photostability [50], BODIPY dyes are proven to be extremely versatile and useful in many biological applications Fig. 11 [68]. 

BODIPY is a short for 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, the basic structure of this type of fluorophore (see Fig. 6.5). Derivatives of this dye have been created by modification of positions 1, 3, 5, 7, and 8, generating an array of fluorophores with very distinct excitation and emission properties [38]. Molecular Probes has synthesized a wide number of BODIPY dyes whose excitation... 

BODIPY fluorophores are a class of probes based on the fused, multi-ring structure, 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (Figure 9.27) (Invitrogen) (U.S. patent 4,774,339). This fundamental molecule can be modified, particularly at its 1, 3, 5, 7, and 8 carbon positions, to produce new fluorophores with different characteristics. The modifications cause spectral shifts in its excitation and emission wavelengths, and can provide sites for chemical coupling to label biomolecules. 

Due to space constraints, only a few review articles that discuss the synthesis and chemistry of novel classes of pyrrole materials will be discussed here. A comprehensive review of the important class of dyes, known collectively as BODIPY dyes (difluoro-4-bora-3a,4a-diaza-.s-indacene 79), appeared <07CRV4891>. Reviews of carboporphyrins <07EJO5461> and acyclic oligopyrroles <07EJO5313> were also published. 

BODIPY FL C3-SE is 4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-propionic acid, succinimidyl ester (Invitrogen). The derivatization to the base BODIPY molecule... 

BODIPY 493/503 C3 Hydrazide 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-propionyl hydrazide MW 334... 

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