Intersystem crossing and triplet excited state properties of thionated naphthalenediimide derivatives

Hussain, Mushraf; Zhao, Jianzhang; Yang, Wenbo; Zhong, Fangfang; Karatay, Ahmet; Yağlıoğlu, H. Gül; Yıldız, Elif Akhüseyin; Hayvalı, Mustafa

doi:10.1016/j.jlumin.2017.06.050

Cited by 42 publications

(39 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For NDI‐Ph and Br‐NDI, excited state absorption (ESA) bands were observed in the 330–500 nm and 550–780 nm range. These ESA bands are characteristics of the T 1 →T n transition of the NDI moiety . The triplet state lifetime of NDI‐Ph was determined as 114.2 μs, and the decay of the triplet state signal is mono‐exponential.…”

Section: Resultsmentioning

confidence: 99%

“…The observed lifetime of the triplet state of the NDI unit in the current dyads is much shorter than the intrinsic triplet state lifetime of the NDI chromophore (ca. 32–276 μs), which is reasonable because the triplet state localized on the NDI can be quenched by the stable radical . This is also proved by measuring the ns TA spectra of NDI‐Ph with increasing concentrations of Ph‐Vz (Supporting Information, Figure S31).…”

Section: Resultsmentioning

confidence: 99%

“…T n transition of the NDIm oiety. [38,39] The triplet state lifetime of NDI-Phw as determined as 114.2 ms, and the decay of the triplet state signal is mono-exponential. No TA signals are ob-…”

Section: Observation Of the Triplet Excited State With Nanosecond Tramentioning

confidence: 99%

See 2 more Smart Citations

Intersystem Crossing in Naphthalenediimide–Oxoverdazyl Dyads: Synthesis and Study of the Photophysical Properties

Hussain

Taddei²,

Bussotti³

et al. 2019

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Oxoverdazyl( Vz) radicalu nits were covalently linked to the naphthalenediimide (NDI) chromophore to study the effect of the radicalo nt he photophysical properties, especially the radicale nhanced intersystem crossing (REISC), which is ap romisinga pproach to develop heavyatom-free triplet photosensitizers. Rigid phenylo re thynylphenyll inkers betweent he two moieties were used, thus REISC andf ormation of doublet (D 1 ,t otal spin quantum number S = 1/2) and quartet states (Q 1 , S = 3/2) are anticipated. The photophysical properties of the dyadsw ere studied with steady-statea nd femtosecond/nanosecond transient absorption (TA) spectroscopiesa nd DFT computations. Femtosecond transienta bsorption spectras how af ast electron transfer (< 150 fs), and ISC (ca. 1.4-1.85ps) is induced by charger ecombination (CR, in toluene). Nanosecond transient absorption spectra demonstrated ab iexponential decay of the triplet state of the NDI moiety.T he fast component (lifetime:5 0ns; population ratio:8 0%)i sa ssigned to the D 1 ! D 0 decay,a nd the slow decay component (2.0 ms; 20 %) to the Q 1 !D 0 ISC. DFT computations indicated ferromagnetic interactions between the radicala nd chromophore( J = 0.07-0.13 eV). Reversible formation of the radical aniono ft he NDI moiety by photoreduction of the radical-NDI dyadsi nt he presence of sacrificial electron donor triethanolamine (TEOA) is achieved. This work is useful for design of new triplet photosensitizers based on the REISC effect.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Intersystem Crossing in Naphthalenediimide–Oxoverdazyl Dyads: Synthesis and Study of the Photophysical Properties

Hussain

Taddei²,

Bussotti³

et al. 2019

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

show abstract

“…The general approach to developing heavy atom-free PSs is to attain a similar energy level of S1 and TSP or proper appropriate molecular geometry to mollify the reserved momentum in ISC. [144] Hussein et al [145] for the first time reported the heavy atom free thionated naphthalenediimide (NDI) derivatives with enhanced ISC and high of Φ Δ of 56% due to 1 (𝜋-𝜋)* → 3 (n-𝜋)* transitioning. Nguyen et al [146] prepared sulphur substituted NDI by one-pot synthesis to achieve enhanced SOC rate and high 1 O 2 generation due to enhancement in electron-donating potential of NDI.…”

Section: Enhanced Intersystem Crossingmentioning

confidence: 99%

Recent Advances in Bio‐Compatible Oxygen Singlet Generation and Its Tumor Treatment

Jin

Fatima

Zhang

et al. 2021

Advanced Therapeutics

View full text Add to dashboard Cite

Light-dependent singlet oxygen ( 1 O 2 ) produced in photodynamic therapy (PDT), is a biologically compatible reactive oxygen species showing the potential to kill tumor cells with fewer side effects on nearby normal healthy cells. The development of a high 1 O 2 generating photosensitizer is a particularly demanding research areas. Based on Jablonski's diagram, the photophysical factors influencing the generation of 1 O 2 are intersystem crossing, triplet quantum yield and life, and the singlet-triplet energy gap. Moreover, nanocarriers are also an emerging research topic with enhanced/localized delivery of photosensitizers to improve the dosage of light and enriched production of 1 O 2 . In this review, the production principle of 1 O 2 in PDT and its killing mechanism with respect to tumor cells are reviewed. In addition, the progress of PDT has been supplemented in clinical applications in recent years and the emergent preclinical tactics for prospective solutions to these challenges are discussed to improve the effectiveness and usefulness of these procedures. Moreover, the remaining research gaps and future work is outlined. This review is anticipated to heighten the research for developing new strategies for modulating the photophysical properties and improved the delivery of photosensitizers.

show abstract

“…It is widely known that chromophores with carbonyl groups such as benzophenone exhibit high ISC efficiency  ISC even without heavy metals due to the large spin-orbit coupling (SOC) caused by the distinct change in orbital symmetry during the transition from the n-π*/π-π* singlet state to the π-π*/n-π* triplet state. [20,[30][31][32][33][34][35][36][37] Ketocoumarin derivatives have also been used as heavy metal-free triplet sensitizers with such characteristics. [30][31][32][33] Among the reported ketocoumarin derivatives, we focused on CBDAC because of its large absorption coefficient in the visible region over 70,000 M -1 cm -1 and weak absorption in the UV region, [30][31][32][33] and it has been reported to have a high  ISC of 92% in benzene.…”

mentioning

confidence: 99%

Heavy metal-free visible-to-UV photon upconversion with over 20% efficiency sensitized by a ketocoumarin derivative

Uji

Harada

Kimizuka

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

Intersystem crossing and triplet excited state properties of thionated naphthalenediimide derivatives

Cited by 42 publications

References 25 publications

Intersystem Crossing in Naphthalenediimide–Oxoverdazyl Dyads: Synthesis and Study of the Photophysical Properties

Intersystem Crossing in Naphthalenediimide–Oxoverdazyl Dyads: Synthesis and Study of the Photophysical Properties

Recent Advances in Bio‐Compatible Oxygen Singlet Generation and Its Tumor Treatment

Heavy metal-free visible-to-UV photon upconversion with over 20% efficiency sensitized by a ketocoumarin derivative

Contact Info

Product

Resources

About