Synthesis, structure, and spectral, electrochemical and fluoride sensing properties of meso-pyrrolyl boron dipyrromethene

Abstract

meso-Pyrrolyl boron dipyrromethene (BODIPY) was prepared under simple reaction conditions by using commercially available chemicals. Prior to this work, the BODIPY compound was prepared in multiple steps by using precursors which were not readily available. The X-ray structure of BODIPY revealed that the meso-pyrrole ring is tilted towards the BF2-dipyrrin moiety with a dihedral angle of 33.94°. The reactivity of the meso-pyrrole ring of BODIPY was tested by subjecting it to bromination and formylation reactions, which afforded (α-bromopyrrolyl) BODIPY and (α-formylpyrrolyl) BODIPY in decent yields. The (α-formylpyrrolyl) BODIPY was used to prepare the pyrrole bridged BODIPY dyad. The pyrrole bridged BODIPY dyad exhibited a 15-20 nm bathochromic shift in the absorption band and was weakly fluorescent compared to meso-pyrrolyl BODIPY. Furthermore, our studies show that the meso-pyrrolyl BODIPY can be used as a specific sensor for F(-) ions because of the presence of meso-pyrrole NH which is involved in interactions with F(-) ions. To prove that meso-pyrrole NH is involved in sensing F(-) ions, we also prepared meso-(N-methylpyrrolyl)-BODIPY and characterized it by various spectroscopic techniques and crystallography. Our studies reveal that meso-(N-methylpyrrolyl)-BODIPY does not sense F(-) ions, supporting the involvement of meso-pyrrole NH in sensing F(-) ions.

Covalently Linked meso‐BODIPYnyl Dithiahomoporphyrins: Synthesis and Properties

“…[5] Synthesis of Tetrapyrrane 7: The required tripyrrane, 7 as E/Z mixture (pale yellow semi solid) was synthesized from diol 6 and excess pyrrole by following our previously reported procedure. [8][9][10][11] The spectroscopic data is in good agreement with the reported data for the BODIPY precursors (8-10). [8][9][10][11] The spectroscopic data is in good agreement with the reported data for the BODIPY precursors (8-10).…”

“…The required diol 6 (E/Z mixture) [5] and tetrapyrrane 7 (E/Z mixture) [7] were synthesized over sequence of steps by following our reported procedures. Different formyl-BODIPY precursors (8)(9)(10)(11) and -dipyrromethanyl aza-BODIPY (12) were synthesized by following the reported protocols. [8][9][10][11][12] As shown in Scheme 1a, the appropriate formyl-BODIPY such as meso-(4formyl phenyl) BODIPY (8), -formyl meso-anisyl BODIPY (9), meso-(2-formyl pyrrolyl) BODIPY (10) and α-(2-formyl-pyrrolyl) BODIPY (11) was treated with equimolar tetrapyrrane 7 in CH 2 Cl 2 in the presence of catalytic amount of BF 3 .OEt 2 at room temperature under inert atmosphere for 15-20 min followed by oxidation with 2 equiv.…”

Assay of fluoride by a novel organic–inorganic mesoporous nano‐sized sensor

“…Although a large number of signals could be used for recognition, fluorescence still emerges as the most powerful transduction way to indicate the chemical sensing events (3,4). The design of fluoride sensor will be particularly challenging due to the significance of this anion in health, environment and medical applications (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). Especially, the increasing interests in the fabrication of anion fluorescent sensors have been concentrated on different related fields.…”

“…Especially, the increasing interests in the fabrication of anion fluorescent sensors have been concentrated on different related fields. The design of fluoride sensor will be particularly challenging due to the significance of this anion in health, environment and medical applications (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). Currently, numerous reports have been carried out for the rational design of organic dyes and supramolecular structures.…”

Synthesis and fluorescence properties of a boron-dipyrrin functionalized perylenediimide derivative

“…[27][28][29] Several dual-channelbased probes for Hg 2+ and other ions have been reported. [30][31] For example, Dipyrromethene boron difluoride (BODIPY)-based dyes have obtained widespread concerns as dual-channel fluorescent probes, [32][33] because of their remarkable properties, including high extinction coefficients, high quantum yields, intense absorption, low citotoxicity and good solubilities in many solvent systems [ [34][35][36][37][38][39][40][41][42].…”