Poly(BODIPY)s: A New Class of Tunable Polymeric Dyes

Abstract

We present a new class of polymeric dyes bearing the difluoroboraindacene (BODIPY) chromophore within the main chain. Starting from a diiodinated BODIPY monomer, homo-and copolymers with a fully conjugated backbone were efficiently synthesized by transition-metal-catalyzed polycondensation reactions. The photophysical properties of the resulting polymeric materials were investigated in bulk and at the single molecule level. It was found that the BODIPY homopolymer resembles the absorption and emission properties of the individual BODIPY chromophore. In contrast, the copolymer products of 1,4-diethynylbenzene and benzene exhibit absorption and emission spectra that are shifted hypsochromically and bathochromically in regard to the homopolymer, respectively, allowing for easy color tuning by the choice of comonomers. The fluorescence quantum yield of the BODIPY homopolymer is remarkably high (57%). The exceptional brightness of the materials was confirmed in the single molecule investigations; the BODIPY homopolymer emitted several times more photons than the well-established fluorescent probe Rhodamine 6G with a quantum yield close to unity.

Three-color Förster resonance energy transfer within single F[sub O]F[sub 1]-ATP synthases: monitoring elastic deformations of the rotary double motor in real time

“…A custom-made confocal microscope setup based on an Olympus IX 71 was used 40,41 for the triple-FRET measurements with single F O F 1 -ATP synthases. Three different lasers were applied: two fiber coupled picosecond pulsed lasers with arbitrary repetition rates up to 80 MHz at 488 nm (PicoTa 490, Picoquant) and 635 nm (LDH-P-635B, Picoquant) were used, and the third, continuous wave laser at 532 nm (compass 315, Coherent) was switched by a fast acusto optical modulator (AOM type 335-192, Crystal Technologies).…”

“…Detection efficiencies of the fluorophores were computed by multiplying the spectral filter characteristics of beam splitters, dichroics, interference filters and the spectral sensitivity of the APDs with the fluorescence spectra of the dyes as described previously. 31,40 The correction factor γ ¼ ðη A · ϕ A Þ∕ðη D · ϕ D Þ comprises both detection efficiencies and quantum yields. Thus, we determined the FRET efficiency E FRET ¼ I ðCy5Þ ∕ðI ðCy5Þ þ γI ðAlexa532Þ Þ quantitatively using the calculated correction factor γ ¼ 0.77.…”

Targeting cytochrome C oxidase in mitochondria with Pt(II)-porphyrins for photodynamic therapy

“…For confocal single-molecule imaging and localization in living cells, bright fluorophores with exceptional photo stability are required 19 . Thus new ultrastable dyes and fluorescent nanocrystals are continuously developed [20][21][22][23] . These fluorophores emit bursts of photons, which yield diffusion properties, association status and conformational changes in vitro and in vivo by fluorescence correlation spectroscopy [24][25][26][27][28] .…”

Polymers and Dyes: Developments and Applications

“…In one study, a di-iodinated derivative of difluoroboraindacene was prepared [67]. Homopolymerization of this molecule was conducted according to the protocol of Yamamoto, while use of 1,4-diethynylbenzene and benzene-(1,4)-diboronic acid enabled copolymerization via Sonogashira and Suzuki coupling, respectively.…”