NIR Absorbing AzaBODIPY Dyes for pH Sensing
- Kubheka, Gugu, Mack, John, Nyokong, Tebello, Zhen, Shen
- Authors: Kubheka, Gugu , Mack, John , Nyokong, Tebello , Zhen, Shen
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186668 , vital:44523 , xlink:href="https://doi.org/10.3390/molecules25163689"
- Description: Two near-infrared (NIR) absorbing di(thien-2-nyl)-di(dimethylanilino)azaBODIPY dyes 2a and 2b were synthesized and characterized that differ depending on whether the dimethylaniline substituents are introduced at the 3,5- or 1,7-positions of the azaBODIPY core. The main spectral bands lie at 824 and 790 nm, respectively, in CH2Cl2. The effect of substituent position on the photophysical and pH sensing properties was analyzed through a comparison of the optical properties with the results of time-dependent density functional theory (TD-DFT) calculations. Protonation of the dimethylamino nitrogen atoms eliminates the intramolecular charge transfer properties of these compounds, and this results in a marked blue-shift of the main absorption bands to 696 and 730 nm, respectively, in CH2Cl2, and a fluorescence “turn-on” effect in the NIR region. The pH dependence studies reveal that the pKa values of the non-protonated 2a and 2b molecules are ca. 6.9 (±0.05) and 7.3 (±0.05), respectively, while that of the monoprotonated species for both dyes is ca. 1.4 (±0.05) making them potentially suitable for use as colorimetric pH indicators under highly acidic conditions.
- Full Text:
- Date Issued: 2020
- Authors: Kubheka, Gugu , Mack, John , Nyokong, Tebello , Zhen, Shen
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186668 , vital:44523 , xlink:href="https://doi.org/10.3390/molecules25163689"
- Description: Two near-infrared (NIR) absorbing di(thien-2-nyl)-di(dimethylanilino)azaBODIPY dyes 2a and 2b were synthesized and characterized that differ depending on whether the dimethylaniline substituents are introduced at the 3,5- or 1,7-positions of the azaBODIPY core. The main spectral bands lie at 824 and 790 nm, respectively, in CH2Cl2. The effect of substituent position on the photophysical and pH sensing properties was analyzed through a comparison of the optical properties with the results of time-dependent density functional theory (TD-DFT) calculations. Protonation of the dimethylamino nitrogen atoms eliminates the intramolecular charge transfer properties of these compounds, and this results in a marked blue-shift of the main absorption bands to 696 and 730 nm, respectively, in CH2Cl2, and a fluorescence “turn-on” effect in the NIR region. The pH dependence studies reveal that the pKa values of the non-protonated 2a and 2b molecules are ca. 6.9 (±0.05) and 7.3 (±0.05), respectively, while that of the monoprotonated species for both dyes is ca. 1.4 (±0.05) making them potentially suitable for use as colorimetric pH indicators under highly acidic conditions.
- Full Text:
- Date Issued: 2020
Optical limiting properties of 3, 5-dipyrenylvinyleneBODIPY dyes at 532 nm
- Kubheka, Gugu, Sanusi, Kayode, Mack, John, Nyokong, Tebello
- Authors: Kubheka, Gugu , Sanusi, Kayode , Mack, John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/237938 , vital:50567 , xlink:href="https://doi.org/10.1016/j.saa.2017.10.021"
- Description: The optical limiting (OL) properties of 3,5-dipyrenylvinyleneBODIPY dyes that contain both electron withdrawing and donating moieties have been investigated by using the z-scan technique at 532 nm in the nanosecond pulse range. The extension of the π-conjugation at the 3,5-positions with pyrenylvinylene groups results in a ca. 200 nm red shift of the main BODIPY spectral band to ca. 700 nm, so there is relatively weak absorbance at 532 nm under ambient light conditions. Reverse saturable absorbance (RSA) profiles are observed in response to incident pulsed laser light that is consistent with a two photon absorption-assisted excited state absorption (ESA) mechanism in CH2Cl2 solution and when the dyes are embedded in poly(bisphenol carbonate A) (PBC) polymer thin films. This demonstrates that 3,5-divinyleneBODIPY dyes are potentially suitable for use in OL applications, since limiting threshold fluence (Ilim) values of below 0.95 J cm−2 are observed when thin films are prepared.
- Full Text:
- Date Issued: 2018
- Authors: Kubheka, Gugu , Sanusi, Kayode , Mack, John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/237938 , vital:50567 , xlink:href="https://doi.org/10.1016/j.saa.2017.10.021"
- Description: The optical limiting (OL) properties of 3,5-dipyrenylvinyleneBODIPY dyes that contain both electron withdrawing and donating moieties have been investigated by using the z-scan technique at 532 nm in the nanosecond pulse range. The extension of the π-conjugation at the 3,5-positions with pyrenylvinylene groups results in a ca. 200 nm red shift of the main BODIPY spectral band to ca. 700 nm, so there is relatively weak absorbance at 532 nm under ambient light conditions. Reverse saturable absorbance (RSA) profiles are observed in response to incident pulsed laser light that is consistent with a two photon absorption-assisted excited state absorption (ESA) mechanism in CH2Cl2 solution and when the dyes are embedded in poly(bisphenol carbonate A) (PBC) polymer thin films. This demonstrates that 3,5-divinyleneBODIPY dyes are potentially suitable for use in OL applications, since limiting threshold fluence (Ilim) values of below 0.95 J cm−2 are observed when thin films are prepared.
- Full Text:
- Date Issued: 2018
Aza boron-pyridyl-isoindoline analogues
- Zhang, Hui, Wu, Yanping, Fan, Minhui, Xiao, Xuqiong, Mack, John, Kubheka, Gugu, Nyokong, Tebello, Lu, Hua
- Authors: Zhang, Hui , Wu, Yanping , Fan, Minhui , Xiao, Xuqiong , Mack, John , Kubheka, Gugu , Nyokong, Tebello , Lu, Hua
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/232912 , vital:50037 , xlink:href="https://doi.org/10.1039/C7NJ00707H"
- Description: Several aza boron-pyridyl-isoindoline analogues are synthesized through a facile and scale-up two step reaction using 1,2-naphthalenedicarbonitrile as a starting material. These analogues show broad envelopes of intense vibrational bands in the absorption spectra with moderate fluorescence quantum yields in solution and the solid-state. An analysis of the structure–property relationships is described based on X-ray crystallography, optical spectroscopy, and theoretical calculations.
- Full Text:
- Date Issued: 2017
- Authors: Zhang, Hui , Wu, Yanping , Fan, Minhui , Xiao, Xuqiong , Mack, John , Kubheka, Gugu , Nyokong, Tebello , Lu, Hua
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/232912 , vital:50037 , xlink:href="https://doi.org/10.1039/C7NJ00707H"
- Description: Several aza boron-pyridyl-isoindoline analogues are synthesized through a facile and scale-up two step reaction using 1,2-naphthalenedicarbonitrile as a starting material. These analogues show broad envelopes of intense vibrational bands in the absorption spectra with moderate fluorescence quantum yields in solution and the solid-state. An analysis of the structure–property relationships is described based on X-ray crystallography, optical spectroscopy, and theoretical calculations.
- Full Text:
- Date Issued: 2017
Optical limiting properties of 2, 6-dibromo-3, 5-distyrylBODIPY dyes at 532 nm
- Kubheka, Gugu, Mack, John, Kobayashi, Nagao, Kimura, Mitsumi, Nyokong, Tebello
- Authors: Kubheka, Gugu , Mack, John , Kobayashi, Nagao , Kimura, Mitsumi , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/190405 , vital:44991 , xlink:href="https://doi.org/10.1142/S1088424617500511"
- Description: Optical limiting properties of 2,6-dibromo-3,5-distyrylBODIPY dyes were investigated by using the z-scan technique at 532 nm in the nanosecond pulse range. A strong reverse saturable absorption response was observed even in solution, which suggests that compounds of this type are potentially suitable for use in optical limiting applications.
- Full Text:
- Date Issued: 2017
- Authors: Kubheka, Gugu , Mack, John , Kobayashi, Nagao , Kimura, Mitsumi , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/190405 , vital:44991 , xlink:href="https://doi.org/10.1142/S1088424617500511"
- Description: Optical limiting properties of 2,6-dibromo-3,5-distyrylBODIPY dyes were investigated by using the z-scan technique at 532 nm in the nanosecond pulse range. A strong reverse saturable absorption response was observed even in solution, which suggests that compounds of this type are potentially suitable for use in optical limiting applications.
- Full Text:
- Date Issued: 2017
Optical limiting properties of 3, 5-diphenyldibenzo-azaBODIPY at 532 nm
- Kubheka, Gugu, Achadu, Ojodomo J, Mack, John, Nyokong, Tebello
- Authors: Kubheka, Gugu , Achadu, Ojodomo J , Mack, John , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/232761 , vital:50022 , xlink:href="https://doi.org/10.1039/C7NJ01503H"
- Description: Optical limiting properties of 3,5-diphenyldibenzo-azaBODIPY were investigated by using the z-scan technique at 532 nm in the nanosecond pulse range and a strong reverse saturable absorption (RSA) response was observed, which can be readily attributed to a two-photon absorption (TPA) assisted excited state absorption (ESA) mechanism in the singlet manifold based on a consideration of the other photophysical properties. The effect of solvent and incorporation into polymer thin films has been investigated in depth. The results indicate that the selection of solvents that enhance the population of the S1 excited state on the nanosecond timescale or embedding the azaBODIPY dye into polymer thin films significantly improves the optical limiting properties.
- Full Text:
- Date Issued: 2017
- Authors: Kubheka, Gugu , Achadu, Ojodomo J , Mack, John , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/232761 , vital:50022 , xlink:href="https://doi.org/10.1039/C7NJ01503H"
- Description: Optical limiting properties of 3,5-diphenyldibenzo-azaBODIPY were investigated by using the z-scan technique at 532 nm in the nanosecond pulse range and a strong reverse saturable absorption (RSA) response was observed, which can be readily attributed to a two-photon absorption (TPA) assisted excited state absorption (ESA) mechanism in the singlet manifold based on a consideration of the other photophysical properties. The effect of solvent and incorporation into polymer thin films has been investigated in depth. The results indicate that the selection of solvents that enhance the population of the S1 excited state on the nanosecond timescale or embedding the azaBODIPY dye into polymer thin films significantly improves the optical limiting properties.
- Full Text:
- Date Issued: 2017
Optical Limiting Properties of 3, 5-Dithienylenevinylene BODIPY Dyes at 532 nm
- Harris, Jessica, Gai, Lizhi, Kubheka, Gugu, Mack, John, Nyokong, Tebello, Shen, Zhen
- Authors: Harris, Jessica , Gai, Lizhi , Kubheka, Gugu , Mack, John , Nyokong, Tebello , Shen, Zhen
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/189274 , vital:44833 , xlink:href="https://doi.org/10.1002/chem.201702503"
- Description: The optical limiting properties of a series of near infrared absorbing 3,5-dithienylenevinylene BODIPY (borondipyrromethene) dyes (1–3) that contain donor and acceptor moieties in their p-conjugation systems were studied by using the z-scan technique at 532 nm in the nanosecond pulse range. A strong reverse saturable absorption response was observed when the compounds are embedded into poly(bisphenol carbonate A) polymer thin films, which demonstrates that BODIPY dyes with this type of structure are suitable for use in optical limiting applications.
- Full Text:
- Date Issued: 2017
- Authors: Harris, Jessica , Gai, Lizhi , Kubheka, Gugu , Mack, John , Nyokong, Tebello , Shen, Zhen
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/189274 , vital:44833 , xlink:href="https://doi.org/10.1002/chem.201702503"
- Description: The optical limiting properties of a series of near infrared absorbing 3,5-dithienylenevinylene BODIPY (borondipyrromethene) dyes (1–3) that contain donor and acceptor moieties in their p-conjugation systems were studied by using the z-scan technique at 532 nm in the nanosecond pulse range. A strong reverse saturable absorption response was observed when the compounds are embedded into poly(bisphenol carbonate A) polymer thin films, which demonstrates that BODIPY dyes with this type of structure are suitable for use in optical limiting applications.
- Full Text:
- Date Issued: 2017
Synthesis and photophysicochemical properties of BODIPY dye functionalized gold nanorods for use in antimicrobial photodynamic therapy
- Kubheka, Gugu, Uddin, Imran, Amuhaya, Edith K, Mack, John, Nyokong, Tebello
- Authors: Kubheka, Gugu , Uddin, Imran , Amuhaya, Edith K , Mack, John , Nyokong, Tebello
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/239897 , vital:50778 , xlink:href="https://doi.org/10.1142/S108842461650070X"
- Description: A series of boron dipyrromethene (BODIPY) dyes with properties that are ideal for a good photosensitizer have been prepared. Functionalization with bromine atoms and attachment to gold nanoparticles through a meso-aniline group results in high singlet oxygen quantum yields and low fluorescent quantum yields. Molecular modelling was used to analyze trends in the MO energies of various brominated aniline BODIPY dyes.
- Full Text:
- Date Issued: 2016
- Authors: Kubheka, Gugu , Uddin, Imran , Amuhaya, Edith K , Mack, John , Nyokong, Tebello
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/239897 , vital:50778 , xlink:href="https://doi.org/10.1142/S108842461650070X"
- Description: A series of boron dipyrromethene (BODIPY) dyes with properties that are ideal for a good photosensitizer have been prepared. Functionalization with bromine atoms and attachment to gold nanoparticles through a meso-aniline group results in high singlet oxygen quantum yields and low fluorescent quantum yields. Molecular modelling was used to analyze trends in the MO energies of various brominated aniline BODIPY dyes.
- Full Text:
- Date Issued: 2016
Synthesis, Characterization, and Electronic Structures of Porphyrins Fused with Polycyclic Aromatic Ring Systems
- Okujima, Tetsuo, Mack, John, Nakamura, Jun, Kubheka, Gugu, Nyokong, Tebello, Zhu, Hua, Komobuchi, Naoki, Ono, Noboru, Yamada, Hiroko, Uno, Hidemitsu, Kobayashi, Nagao
- Authors: Okujima, Tetsuo , Mack, John , Nakamura, Jun , Kubheka, Gugu , Nyokong, Tebello , Zhu, Hua , Komobuchi, Naoki , Ono, Noboru , Yamada, Hiroko , Uno, Hidemitsu , Kobayashi, Nagao
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/240360 , vital:50827 , xlink:href="https://doi.org/10.1002/chem.201602213"
- Description: A series of porphyrins fused with acenaphthylene, phenanthroline, and benzofluoranthene polycyclic aromatic rings were prepared by means of a 3+1 porphyrin synthesis approach and subsequent retro-Diels–Alder reaction of bicyclo[2.2.2]octadiene-fused precursors. Analysis of the magnetic circular dichroism spectra and the results of time-dependent DFT calculations are used to identify the reasons for the trends observed in the wavelengths and relative intensities of the Q bands of the products. Michl's perimeter model is used as a conceptual framework to explain the changes in the relative energies of the frontier π-molecular orbitals.
- Full Text:
- Date Issued: 2016
- Authors: Okujima, Tetsuo , Mack, John , Nakamura, Jun , Kubheka, Gugu , Nyokong, Tebello , Zhu, Hua , Komobuchi, Naoki , Ono, Noboru , Yamada, Hiroko , Uno, Hidemitsu , Kobayashi, Nagao
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/240360 , vital:50827 , xlink:href="https://doi.org/10.1002/chem.201602213"
- Description: A series of porphyrins fused with acenaphthylene, phenanthroline, and benzofluoranthene polycyclic aromatic rings were prepared by means of a 3+1 porphyrin synthesis approach and subsequent retro-Diels–Alder reaction of bicyclo[2.2.2]octadiene-fused precursors. Analysis of the magnetic circular dichroism spectra and the results of time-dependent DFT calculations are used to identify the reasons for the trends observed in the wavelengths and relative intensities of the Q bands of the products. Michl's perimeter model is used as a conceptual framework to explain the changes in the relative energies of the frontier π-molecular orbitals.
- Full Text:
- Date Issued: 2016
Synthesis, characterization and photodynamic therapy properties of an octa-4-tert-butylphenoxy-substituted phosphorus (V) triazatetrabenzcorrole
- Shi, Maohu, Tian, Jiangwei, Mkhize, Colin, Kubheka, Gugu, Zhou, Jinfeng, Mack, John, Nyokong, Tebello, Shen, Zhen
- Authors: Shi, Maohu , Tian, Jiangwei , Mkhize, Colin , Kubheka, Gugu , Zhou, Jinfeng , Mack, John , Nyokong, Tebello , Shen, Zhen
- Date: 2014
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/241494 , vital:50944 , xlink:href="https://doi.org/10.1142/S1088424614500436"
- Description: A novel octa-4-tert-butylphenoxy-substituted phosphorus(V) triazatetrabenzcorrole (PVTBC), has been synthesized and characterized by MALDI-TOF MS and NMR, FT-IR and MCD spectroscopy. The fluorescence emission spectrum was used to determine the fluorescence quantum yield and the quantum yield for singlet oxygen generation was calculated by using 1,3-diphenylisobenzofuran as a scavenger. The photocytoxicity against U87MG cells was measured. The results indicated that PVTBC is potentially useful as an NIR region photosensitizer for photodynamic therapy (PDT).
- Full Text:
- Date Issued: 2014
- Authors: Shi, Maohu , Tian, Jiangwei , Mkhize, Colin , Kubheka, Gugu , Zhou, Jinfeng , Mack, John , Nyokong, Tebello , Shen, Zhen
- Date: 2014
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/241494 , vital:50944 , xlink:href="https://doi.org/10.1142/S1088424614500436"
- Description: A novel octa-4-tert-butylphenoxy-substituted phosphorus(V) triazatetrabenzcorrole (PVTBC), has been synthesized and characterized by MALDI-TOF MS and NMR, FT-IR and MCD spectroscopy. The fluorescence emission spectrum was used to determine the fluorescence quantum yield and the quantum yield for singlet oxygen generation was calculated by using 1,3-diphenylisobenzofuran as a scavenger. The photocytoxicity against U87MG cells was measured. The results indicated that PVTBC is potentially useful as an NIR region photosensitizer for photodynamic therapy (PDT).
- Full Text:
- Date Issued: 2014
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