Structural modification strategies for the rational design of red/NIR region BODIPYs

Lü, Hua; Mack, John; Yang, Yongchao; Shen, Zhen

doi:10.1039/c4cs00030g

Cited by 1,153 publications

(722 citation statements)

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“…6 Unmodied BODIPY absorbs and emits light at wavelengths in the visible spectral region ($500 nm). Through chemical modication, BODIPY absorption and emission can be shied toward lower energy by (1) appending p-conjugated groups, at the C1, C2 or C6, C7 positions of pyrrole units, hence extending p-conjugation of the system; (2) fusing an aromatic ring with the dipyrrane core by an intramolecular oxidative cyclohydrogenation; (3) direct functionalization by introduction of aryl group through double or triple bond into 2,6-positions (4) replacing carbon C8 with a nitrogen atom (aza-BODIPY dye family) (5) functionalizing at C3, C5 or C8 -positions to obtain aryl-, styryl-or alkynyl-substituted BODIPYs.…”

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Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole–BODIPY donor–acceptor systems

et al. 2016

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(2016). Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole-BODIPY donor-acceptor systems. RSC Advances: an international journal to further the chemical sciences, 6 (43), 36500-36509.Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole-BODIPY donor-acceptor systems Abstract Synthesis, spectral and electrochemical properties of a series of new panchromatic BODIPY donor-acceptordonor derivatives, comprising carbazole conjugated with systematically elongated framework by thiophenebased linkers were investigated. It has been found that elongation of the π-system with one thiophene unit shifts the spectra toward near infrared, while incorporation of next thiophene derivatives has only limited influence on the lowest energy transition, causing no further shift of absorption maxima. Elongation of π-conjugation of the donor arm tunes the electron properties, influencing the ionization potential (IP) and electron affinity (EA) values of the molecules. The experimental results are supported by quantum chemical computations revealing that electron density of SOMO orbital is low at the 3-positions of terminal carbazole units in BODIPY push-pull oligomers while elongating their backbone, thus preventing them to undergo electrochemical polymerization giving reversibly p-and n-dopable products. Presented study tests the influence and limitations of incorporation of electron-rich substituents for designing panchromatic BODIPY systems. elongating their backbone, thus preventing them to undergo electrochemical polymerization giving reversibly p-and n-dopable products. Presented study tests the influence and limitations of incorporation of electron -rich substituents for designing panchromatic BODIPY systems.

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Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole–BODIPY donor–acceptor systems

et al. 2016

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“…MO calculations have demonstrated that there is a marked red-shift of the main spectral bands of aza-BODIPY dyes, since the LUMO has a large MO coefficient on the aza-nitrogen atom and this results in a marked narrowing of the HOMO-LUMO gap relative to the analogous BODIPYs (Figure 6). 11 The most important optical and photophysical properties of BODIPY dyes are retained, and so these compounds are potentially suitable for use in biomedical applications in the biological window. In a similar manner to what has been reported for fused-ring-expanded Pc analogues (Figures 2 and 3), significant issues were encountered with compound stability when 2,3-naphtho moieties were introduced at the pyrrole β -carbons.…”

Section: Resultsmentioning

confidence: 99%

TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications

Mack¹,

Wildervanck

Nyokong

2014

Turk J Chem

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Geometry optimizations and TD-DFT calculations have been carried out on series of fused-ring-expanded phthalonitriles, phthalocyanines, and aza-dipyrromethene boron difluoride (aza-BODIPY) dyes and trends in their optical and redox properties have been analyzed. The potential utility of fused-ring-expanded phthalocyanine and aza-BODIPY analogues for photodynamic therapy and near infrared region sensor applications is assessed on this basis. Recent attempts to prepare fused-ring-expanded aza-BODIPY analogues with benzene, pyrazine, and naphthalene rings have demonstrated that the properties of aza-BODIPYs vary markedly when different fused ring systems are added to the β -carbons of the pyrrole rings. A comparison of the TD-DFT calculations demonstrates that, as has previously been postulated, trends in the optical spectra, redox properties, and electronic structures of aza-BODIPYs follow those observed for the phthalonitrile precursors and the analogous phthalocyanines despite the absence of a fully conjugated macrocyclic perimeter that obeys Hückel's rule.

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“…These chemosensors are generally chromogenic and/or fluorescent probes, which efficiently change their photophysical properties in the presence of anions. Among numerous fluorophores, BODIPY dyes possess excellent photophysical properties and applications in the areas of anion sensors, metal probes, and pH indicators [14][15][16][17][18][19][20] . This versatile utility is due to the capacity to substitute the many positions of the BODIPY core in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

A Bodipy-Phenol-Based Sensor for Selectively Recognizing Three Basic Anions

Wei

Xie

2015

J. Chil. Chem. Soc.

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A novel BODIPY-based anion sensor 1 bearing di-tert-butyl phenol unit was designed and prepared. In the presence of three basic anions F -, AcO -or H 2 PO 4 -, 1 exhibited two novel partially overlapped red-shift absorption bands at 718 nm and 757 nm, respectively. The formation of allotropic structures, after deprotonation of phenol OH, is responsible for these two emerging bands. Fluorescence quenching was also observed due to intramolecular charge transfer (ICT) from phenolate to BODIPY core. As results revealed, the anion affinity mainly depended on the acidity of binding site OH and the basicity of the target anion. Moreover, two bulky tert-butyl groups cannot effectively exclude the approach of large anions to phenol OH, but can facilitate the formation of allotropic resonance structures.

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Structural modification strategies for the rational design of red/NIR region BODIPYs

Cited by 1,153 publications

References 358 publications

Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole–BODIPY donor–acceptor systems

Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole–BODIPY donor–acceptor systems

TD-DFT calculations and MCD spectroscopy of porphyrin and phthalocyanine analogues: rational design of photosensitizers for PDT and NIR region sensor applications

A Bodipy-Phenol-Based Sensor for Selectively Recognizing Three Basic Anions

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