Examination of Chlorin–Bacteriochlorin Energy‐transfer Dyads as Prototypes for Near‐infrared Molecular Imaging Probes<sup>†</sup>

Kee, Hooi Ling; Nothdurft, Ralph; Muthiah, Chinnasamy; Diers, James R.; Fan, Dazhong; Ptaszek, Marcin; Bocian, David F.; Lindsey, Jonathan S.; Culver, Joseph P.; Holten, Dewey

doi:10.1111/j.1751-1097.2008.00409.x

Cited by 52 publications

(74 citation statements)

References 68 publications

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“…Chlorin–bacteriochlorin dyads with a free base chlorin ( Dyad-6a ) 278 or zinc chlorin ( Dyad-6b ) 280 undergo fast and efficient excited-state energy transfer from chlorin to bacteriochlorin. 281 The 3,13-bis(phenylethynyl) substituents on the chlorin impart a bathochromic shift of the longwavelength absorption band.…”

Section: Smorgasbord Of Chlorinsmentioning

confidence: 99%

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De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

2015

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Woodward reported his infamous synthesis of chlorin e 6 trimethyl ester, a known synthetic precursor to chlorophyll a. [59][60][61][62][63][64]124 The work was posited on a half-century of intensive studies by many investigators in tetrapyrrole chemistry and began a decade after the close of Fischer's lifetime of research 125−128 (which included an uncompleted synthetic program directed toward chlorophylls 15 ). Indeed, "he read all the umpteen papers on the chlorophylls written by Willstaẗter and Fischer, including the experimental parts." 129 The Woodward synthesis of chlorin e 6 trimethyl ester required 46 steps, of which 24 were spent on converting the sole precursor, Knorr's pyrrole, to the four pyrroles destined to form rings A−D; 7 additional steps accrued to obtain the dipyrromethanes that constitute the Eastern and Western halves (Scheme 13, the step numbers are identical to those shown in ref 64.). The first step formed the Knorr pyrrole (in several kg quantities), the next 24 steps were divided into four parallel paths, whereas the remaining 21 steps proceeded in linear fashion. Remarkable features of the synthesis include the directed intramolecular joining (via an imine) of the Eastern and Western halves (step 33), construction of the acrylate Scheme 10. Hydrogenation of a Porphyrin to Form a Chlorin Scheme 11. Representative meso-Tetraarylchlorins Scheme 12. Methyl Pyropheophorbide a

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Section: Smorgasbord Of Chlorinsmentioning

confidence: 99%

“…The latter underwent selective zincation of the chlorin to give Dyad-6b given the great disparity in ease of metalation of chlorins versus bacteriochlorins. 280,450 …”

Section: Smorgasbord Of Chlorinsmentioning

confidence: 99%

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

2015

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“…1–7 In ET arrays, excitation energy flows from chromophores with higher excited state energies to that with the lowest energy (terminal acceptor) allowing, for example, construction of fluorophores with a large (pseudo)Stokes’ shift, 2 development of a family of fluorophores with a common excitation wavelength and variable emission bands, 3,4 and fluorophores multiple excitation wavelengths. 5 Of particular interest are ET arrays with acceptors emitting in the deep-red or near-infrared spectral window, as they can be potentially used for deep-tissue in vivo imaging. 3,6 We employed hydroporphyrins (chlorins and bacteriochlorins) as fluorescent entities in energy transfer arrays, due to their favorable properties for certain bioimaging applications.…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

et al. 2017

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BODIPY-hydroporphyrin energy transfer arrays allow for development of family of fluorophores featuring a common excitation band at 500 nm, tunable excitation band in deep red/near-infrared window, and tunable emission. Their biomedical applications are contingent upon retaining their optical properties in aqueous environment. Amphiphilic arrays containing PEG-substituted BODIPY and chlorins or bacteriochlorins were prepared and their optical and fluorescence properties were determined in organic solvents and aqueous surfactants. The first series of arrays contains BODIPYs with PEG substituents attached to the boron, whereas in the second series, PEG substituents are attached to the aryl at the meso positions of BODIPY. For both series of arrays, excitation of BODIPY at 500 nm results in an efficient energy transfer to and bright emission of hydroporphyrin in deep-red (640–660 nm) or near-infrared (740–760 nm) spectral windows. In aqueous non-ionic surfactants (Triton X-100 and Tween 20) arrays from the second series exhibit significant quenching of fluorescence, whereas properties of arrays from the first series are comparable to those observed in polar organic solvents. Reported arrays possess large effective Stokes shift (115 – 260 nm), multiple excitation wavelengths, and narrow, tunable deep-red/near-IR fluorescence in aqueous surfactants, and are promising candidates for a variety of biomedical-related applications.

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“…14 However, there are only a handful of ET arrays with both donor and acceptor absorbing in these spectral windows. 15–18 …”

Section: Introductionmentioning

confidence: 99%

BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands

2017

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A series of energy transfer arrays, comprising of a near-IR absorbing and emitting bacteriochlorin, and BODIPY derivatives with different absorption bands in the visible region (503 – 668 nm) have been synthesized. Absorption band of BODIPY was tuned by installation of 0, 1, or 2 styryl substituents [2-(2,4,6-trimethoxyphenyl)ethenyl], which leads to derivatives with absorption maxima at 503 nm, 587 nm, and 668 nm, respectively Efficient energy transfer (>0.90) is observed for each dyad, which is manifested by nearly exclusive emission from bacteriochlorin moiety upon BODIPY excitation. Fluorescence quantum yield of each dyad in non-polar solvent (toluene) is comparable with that observed for corresponding bacteriochlorin monomer, and is significantly reduced in solvent of high dielectric constants (DMF), most likely by photoinduced electron transfer. Given the availability of diverse BODIPY derivatives, with absorption in 500–700 nm, BODIPY-bacteriochlorin arrays should allow for construction of near-IR emitting agents with multiple and broadly tunable absorption bands. Solvent-dielectric constants dependence of Φf in dyads gives an opportunity to construct environmentally-sensitive fluorophores and probes.

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Examination of Chlorin–Bacteriochlorin Energy‐transfer Dyads as Prototypes for Near‐infrared Molecular Imaging Probes^†

Cited by 52 publications

References 68 publications

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands

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Examination of Chlorin–Bacteriochlorin Energy‐transfer Dyads as Prototypes for Near‐infrared Molecular Imaging Probes†

Cited by 52 publications

References 68 publications

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

De NovoSynthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World

Amphiphilic BODIPY-Hydroporphyrin Energy Transfer Arrays with Broadly Tunable Absorption and Deep Red/Near-Infrared Emission in Aqueous Micelles

BODIPY–Bacteriochlorin Energy Transfer Arrays: Toward Near-IR Emitters with Broadly Tunable, Multiple Absorption Bands

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Examination of Chlorin–Bacteriochlorin Energy‐transfer Dyads as Prototypes for Near‐infrared Molecular Imaging Probes^†