A long-lived charge-separated state of spiro compact electron donor-acceptor dyads based on rhodamine and naphthalenediimide chromophores
Spiro rhodamine (Rho)-naphthalenediimide ( NDI ) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, i.e. to form the 3 CS state, not the 1 CS state, to prolong the CS state lifetime by the electron...
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| Published in | Chemical science (Cambridge) Vol. 13; no. 45; pp. 13426 - 13441 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
23.11.2022
Royal Society of Chemistry The Royal Society of Chemistry |
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| Online Access | Get full text |
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| Abstract | Spiro rhodamine (Rho)-naphthalenediimide (
NDI
) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach,
i.e.
to form the
3
CS state, not the
1
CS state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of
3
CS → S
0
. The electron donor Rho (lactam form) is attached
via
three σ bonds, including two C-C and one N-N bonds (
Rho-NDI
), or an intervening phenylene, to the electron acceptor
NDI
(
Rho-Ph-NDI
and
Rho-PhMe-NDI
). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (<120 fs) occurred to generate an upper triplet state localized on the
NDI
moiety (
3
NDI*), and then to form the CS state. For
Rho-NDI
in both non-polar and polar solvents, a long-lived
3
CS state (lifetime
τ
= 0.13 μs) and charge separation quantum yield (
Φ
CS
) up to 25% were observed, whereas for
Rho-Ph-NDI
(
τ
T
= 1.1 μs) and
Rho-PhMe-NDI
(
τ
T
= 2.0 μs), a low-lying
3
NDI* state was formed by charge recombination (CR) in
n
-hexane (HEX). In toluene (TOL), however, CS states were observed for
Rho-Ph-NDI
(0.37 μs) and
Rho-PhMe-NDI
(0.63 μs). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and
NDI
moieties for
Rho-NDI
was proved. Time-resolved EPR (TREPR) spectra detected two transient species including
NDI
-localized triplets (formed
via
SOC-ISC) and a
3
CS state. The CS state of
Rho-NDI
features the largest dipolar interaction (|
D
| = 184 MHz) compared to
Rho-Ph-NDI
(|
D
| = 39 MHz) and
Rho-PhMe-NDI
(|
D
| = 41 MHz) due to the smallest distance between Rho and
NDI
moieties. For
Rho-NDI
, the time-dependent
e
,
a
→
a
,
e
phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect.
Spiro compact rhodamine-naphthalenediimide electron donor-acceptor dyads show a long-lived charge separated state (lifetime: 0.72 μs) based on the electron spin control effect were reported. |
|---|---|
| AbstractList | Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor–acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, i.e. to form the 3CS state, not the 1CS state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of 3CS → S0. The electron donor Rho (lactam form) is attached via three σ bonds, including two C–C and one N–N bonds (Rho-NDI), or an intervening phenylene, to the electron acceptor NDI (Rho-Ph-NDI and Rho-PhMe-NDI). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (<120 fs) occurred to generate an upper triplet state localized on the NDI moiety (3NDI*), and then to form the CS state. For Rho-NDI in both non-polar and polar solvents, a long-lived 3CS state (lifetime τ = 0.13 μs) and charge separation quantum yield (ΦCS) up to 25% were observed, whereas for Rho-Ph-NDI (τT = 1.1 μs) and Rho-PhMe-NDI (τT = 2.0 μs), a low-lying 3NDI* state was formed by charge recombination (CR) in n-hexane (HEX). In toluene (TOL), however, CS states were observed for Rho-Ph-NDI (0.37 μs) and Rho-PhMe-NDI (0.63 μs). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and NDI moieties for Rho-NDI was proved. Time-resolved EPR (TREPR) spectra detected two transient species including NDI-localized triplets (formed via SOC-ISC) and a 3CS state. The CS state of Rho-NDI features the largest dipolar interaction (|D| = 184 MHz) compared to Rho-Ph-NDI (|D| = 39 MHz) and Rho-PhMe-NDI (|D| = 41 MHz) due to the smallest distance between Rho and NDI moieties. For Rho-NDI, the time-dependent e,a → a,e phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect. Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor–acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, i.e. to form the 3 CS state, not the 1 CS state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of 3 CS → S 0 . The electron donor Rho (lactam form) is attached via three σ bonds, including two C–C and one N–N bonds (Rho-NDI), or an intervening phenylene, to the electron acceptor NDI (Rho-Ph-NDI and Rho-PhMe-NDI). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (<120 fs) occurred to generate an upper triplet state localized on the NDI moiety ( 3 NDI*), and then to form the CS state. For Rho-NDI in both non-polar and polar solvents, a long-lived 3 CS state (lifetime τ = 0.13 μs) and charge separation quantum yield ( Φ CS ) up to 25% were observed, whereas for Rho-Ph-NDI ( τ T = 1.1 μs) and Rho-PhMe-NDI ( τ T = 2.0 μs), a low-lying 3 NDI* state was formed by charge recombination (CR) in n -hexane (HEX). In toluene (TOL), however, CS states were observed for Rho-Ph-NDI (0.37 μs) and Rho-PhMe-NDI (0.63 μs). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and NDI moieties for Rho-NDI was proved. Time-resolved EPR (TREPR) spectra detected two transient species including NDI-localized triplets (formed via SOC-ISC) and a 3 CS state. The CS state of Rho-NDI features the largest dipolar interaction (| D | = 184 MHz) compared to Rho-Ph-NDI (| D | = 39 MHz) and Rho-PhMe-NDI (| D | = 41 MHz) due to the smallest distance between Rho and NDI moieties. For Rho-NDI, the time-dependent e , a → a , e phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect. Spiro compact rhodamine-naphthalenediimide electron donor–acceptor dyads show a long-lived charge separated state (lifetime: 0.72 μs) based on the electron spin control effect were reported. Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, to form the CS state, not the CS state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of CS → S . The electron donor Rho (lactam form) is attached three σ bonds, including two C-C and one N-N bonds (Rho-NDI), or an intervening phenylene, to the electron acceptor NDI (Rho-Ph-NDI and Rho-PhMe-NDI). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (<120 fs) occurred to generate an upper triplet state localized on the NDI moiety ( NDI*), and then to form the CS state. For Rho-NDI in both non-polar and polar solvents, a long-lived CS state (lifetime = 0.13 μs) and charge separation quantum yield ( ) up to 25% were observed, whereas for Rho-Ph-NDI ( = 1.1 μs) and Rho-PhMe-NDI ( = 2.0 μs), a low-lying NDI* state was formed by charge recombination (CR) in -hexane (HEX). In toluene (TOL), however, CS states were observed for Rho-Ph-NDI (0.37 μs) and Rho-PhMe-NDI (0.63 μs). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and NDI moieties for Rho-NDI was proved. Time-resolved EPR (TREPR) spectra detected two transient species including NDI-localized triplets (formed SOC-ISC) and a CS state. The CS state of Rho-NDI features the largest dipolar interaction (| | = 184 MHz) compared to Rho-Ph-NDI (| | = 39 MHz) and Rho-PhMe-NDI (| | = 41 MHz) due to the smallest distance between Rho and NDI moieties. For Rho-NDI, the time-dependent , → , phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect. Spiro rhodamine (Rho)-naphthalenediimide ( NDI ) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, i.e. to form the 3 CS state, not the 1 CS state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of 3 CS → S 0 . The electron donor Rho (lactam form) is attached via three σ bonds, including two C-C and one N-N bonds ( Rho-NDI ), or an intervening phenylene, to the electron acceptor NDI ( Rho-Ph-NDI and Rho-PhMe-NDI ). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (<120 fs) occurred to generate an upper triplet state localized on the NDI moiety ( 3 NDI*), and then to form the CS state. For Rho-NDI in both non-polar and polar solvents, a long-lived 3 CS state (lifetime τ = 0.13 μs) and charge separation quantum yield ( Φ CS ) up to 25% were observed, whereas for Rho-Ph-NDI ( τ T = 1.1 μs) and Rho-PhMe-NDI ( τ T = 2.0 μs), a low-lying 3 NDI* state was formed by charge recombination (CR) in n -hexane (HEX). In toluene (TOL), however, CS states were observed for Rho-Ph-NDI (0.37 μs) and Rho-PhMe-NDI (0.63 μs). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and NDI moieties for Rho-NDI was proved. Time-resolved EPR (TREPR) spectra detected two transient species including NDI -localized triplets (formed via SOC-ISC) and a 3 CS state. The CS state of Rho-NDI features the largest dipolar interaction (| D | = 184 MHz) compared to Rho-Ph-NDI (| D | = 39 MHz) and Rho-PhMe-NDI (| D | = 41 MHz) due to the smallest distance between Rho and NDI moieties. For Rho-NDI , the time-dependent e , a → a , e phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect. Spiro compact rhodamine-naphthalenediimide electron donor-acceptor dyads show a long-lived charge separated state (lifetime: 0.72 μs) based on the electron spin control effect were reported. Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, i.e. to form the 3CS state, not the 1CS state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of 3CS → S0. The electron donor Rho (lactam form) is attached via three σ bonds, including two C-C and one N-N bonds (Rho-NDI), or an intervening phenylene, to the electron acceptor NDI (Rho-Ph-NDI and Rho-PhMe-NDI). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (<120 fs) occurred to generate an upper triplet state localized on the NDI moiety (3NDI*), and then to form the CS state. For Rho-NDI in both non-polar and polar solvents, a long-lived 3CS state (lifetime τ = 0.13 μs) and charge separation quantum yield (Φ CS) up to 25% were observed, whereas for Rho-Ph-NDI (τ T = 1.1 μs) and Rho-PhMe-NDI (τ T = 2.0 μs), a low-lying 3NDI* state was formed by charge recombination (CR) in n-hexane (HEX). In toluene (TOL), however, CS states were observed for Rho-Ph-NDI (0.37 μs) and Rho-PhMe-NDI (0.63 μs). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and NDI moieties for Rho-NDI was proved. Time-resolved EPR (TREPR) spectra detected two transient species including NDI-localized triplets (formed via SOC-ISC) and a 3CS state. The CS state of Rho-NDI features the largest dipolar interaction (|D| = 184 MHz) compared to Rho-Ph-NDI (|D| = 39 MHz) and Rho-PhMe-NDI (|D| = 41 MHz) due to the smallest distance between Rho and NDI moieties. For Rho-NDI, the time-dependent e,a → a,e phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect.Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, i.e. to form the 3CS state, not the 1CS state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of 3CS → S0. The electron donor Rho (lactam form) is attached via three σ bonds, including two C-C and one N-N bonds (Rho-NDI), or an intervening phenylene, to the electron acceptor NDI (Rho-Ph-NDI and Rho-PhMe-NDI). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (<120 fs) occurred to generate an upper triplet state localized on the NDI moiety (3NDI*), and then to form the CS state. For Rho-NDI in both non-polar and polar solvents, a long-lived 3CS state (lifetime τ = 0.13 μs) and charge separation quantum yield (Φ CS) up to 25% were observed, whereas for Rho-Ph-NDI (τ T = 1.1 μs) and Rho-PhMe-NDI (τ T = 2.0 μs), a low-lying 3NDI* state was formed by charge recombination (CR) in n-hexane (HEX). In toluene (TOL), however, CS states were observed for Rho-Ph-NDI (0.37 μs) and Rho-PhMe-NDI (0.63 μs). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and NDI moieties for Rho-NDI was proved. Time-resolved EPR (TREPR) spectra detected two transient species including NDI-localized triplets (formed via SOC-ISC) and a 3CS state. The CS state of Rho-NDI features the largest dipolar interaction (|D| = 184 MHz) compared to Rho-Ph-NDI (|D| = 39 MHz) and Rho-PhMe-NDI (|D| = 41 MHz) due to the smallest distance between Rho and NDI moieties. For Rho-NDI, the time-dependent e,a → a,e phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect. Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor–acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, i.e. to form the 3 CS state, not the 1 CS state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of 3 CS → S 0 . The electron donor Rho (lactam form) is attached via three σ bonds, including two C–C and one N–N bonds (Rho-NDI), or an intervening phenylene, to the electron acceptor NDI (Rho-Ph-NDI and Rho-PhMe-NDI). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (<120 fs) occurred to generate an upper triplet state localized on the NDI moiety ( 3 NDI*), and then to form the CS state. For Rho-NDI in both non-polar and polar solvents, a long-lived 3 CS state (lifetime τ = 0.13 μs) and charge separation quantum yield ( Φ CS ) up to 25% were observed, whereas for Rho-Ph-NDI ( τ T = 1.1 μs) and Rho-PhMe-NDI ( τ T = 2.0 μs), a low-lying 3 NDI* state was formed by charge recombination (CR) in n -hexane (HEX). In toluene (TOL), however, CS states were observed for Rho-Ph-NDI (0.37 μs) and Rho-PhMe-NDI (0.63 μs). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and NDI moieties for Rho-NDI was proved. Time-resolved EPR (TREPR) spectra detected two transient species including NDI-localized triplets (formed via SOC-ISC) and a 3 CS state. The CS state of Rho-NDI features the largest dipolar interaction (| D | = 184 MHz) compared to Rho-Ph-NDI (| D | = 39 MHz) and Rho-PhMe-NDI (| D | = 41 MHz) due to the smallest distance between Rho and NDI moieties. For Rho-NDI, the time-dependent e , a → a , e phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect. Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state based on the electron spin control approach, i.e. to form the (CS)-C-3 state, not the (CS)-C-1 state, to prolong the CS state lifetime by the electron spin forbidden feature of the charge recombination process of (CS)-C-3 -> S-0. The electron donor Rho (lactam form) is attached via three sigma bonds, including two C-C and one N-N bonds (Rho-NDI), or an intervening phenylene, to the electron acceptor NDI (Rho-Ph-NDI and Rho-PhMe-NDI). Transient absorption (TA) spectra show that fast intersystem crossing (ISC) (< 120 fs) occurred to generate an upper triplet state localized on the NDI moiety ((NDI)-N-3*), and then to form the CS state. For Rho-NDI in both non-polar and polar solvents, a long-lived (CS)-C-3 state (lifetime tau = 0.13 mu s) and charge separation quantum yield (phi(CS)) up to 25% were observed, whereas for Rho-Ph-NDI (tau(T) = 1.1 mu s) and Rho-PhMe-NDI (tau(T) = 2.0 mu s), a low-lying (NDI)-N-3* state was formed by charge recombination (CR) in n-hexane (HEX). In toluene (TOL), however, CS states were observed for Rho-Ph-NDI (0.37 mu s) and Rho-PhMe-NDI (0.63 mu s). With electron paramagnetic resonance (EPR) spectra, weak electronic coupling between the Rho and NDI moieties for Rho-NDI was proved. Time-resolved EPR (TREPR) spectra detected two transient species including NDI-localized triplets (formed via SOC-ISC) and a (CS)-C-3 state. The CS state of Rho-NDI features the largest dipolar interaction (|D| = 184 MHz) compared to Rho-Ph-NDI (|D| = 39 MHz) and Rho-PhMe-NDI (|D| = 41 MHz) due to the smallest distance between Rho and NDI moieties. For Rho-NDI, the time-dependent e,a & RARR; a,e phase change of the CS state TREPR spectrum indicates that the long-lived CS state is based on the electron spin control effect. |
| Author | Jiang, Xiao Mohammed, Omar F Kurganskii, Ivan Zhao, Jianzhang Xiao, Xiao Maity, Partha Fedin, Matvey |
| AuthorAffiliation | State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources 3A, and Novosibirsk State University SB RAS Institutskaya Str Key Laboratory of Industrial Ecology and Environmental Engineering (Ministry of Education) School of Environmental Science and Technology School of Chemical Engineering King Abdullah University of Science and Technology (KAUST) College of Chemistry Division of Physical Sciences and Engineering International Tomography Center Frontiers Science Center for Smart Materials Xinjiang University State Key Laboratory of Fine Chemicals Dalian University of Technology |
| AuthorAffiliation_xml | – name: State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources – name: Division of Physical Sciences and Engineering – name: School of Chemical Engineering – name: 3A, and Novosibirsk State University – name: College of Chemistry – name: Frontiers Science Center for Smart Materials – name: Xinjiang University – name: State Key Laboratory of Fine Chemicals – name: Key Laboratory of Industrial Ecology and Environmental Engineering (Ministry of Education) – name: SB RAS Institutskaya Str – name: School of Environmental Science and Technology – name: Dalian University of Technology – name: King Abdullah University of Science and Technology (KAUST) – name: International Tomography Center |
| Author_xml | – sequence: 1 givenname: Xiao surname: Xiao fullname: Xiao, Xiao – sequence: 2 givenname: Ivan surname: Kurganskii fullname: Kurganskii, Ivan – sequence: 3 givenname: Partha surname: Maity fullname: Maity, Partha – sequence: 4 givenname: Jianzhang surname: Zhao fullname: Zhao, Jianzhang – sequence: 5 givenname: Xiao surname: Jiang fullname: Jiang, Xiao – sequence: 6 givenname: Omar F surname: Mohammed fullname: Mohammed, Omar F – sequence: 7 givenname: Matvey surname: Fedin fullname: Fedin, Matvey |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36507154$$D View this record in MEDLINE/PubMed |
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| ISSN | 2041-6520 |
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| Issue | 45 |
| Keywords | TRIPLET-STATES RECOMBINATION DESIGN ENERGY EXCITED-STATE TRANSITION-METAL-COMPLEXES DYNAMICS RADICAL-ION PAIRS DEPENDENCE PERYLENE |
| Language | English |
| License | This journal is © The Royal Society of Chemistry. |
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| Notes | For ESI and crystallographic data in CIF or other electronic format see 2190442 https://doi.org/10.1039/d2sc04258d Electronic supplementary information (ESI) available: General experimental methods, synthesis of compounds, molecular structure characterization, X-ray crystallographic data, computational details and additional spectra. CCDC ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 These authors contributed equally to this work. |
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| SSID | ssj0000331527 |
| Score | 2.472245 |
| Snippet | Spiro rhodamine (Rho)-naphthalenediimide (
NDI
) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state... Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor–acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state... Spiro rhodamine (Rho)-naphthalenediimide (NDI) electron donor-acceptor orthogonal dyads were prepared to generate a long-lived charge separation (CS) state... |
| Source | Web of Science |
| SourceID | pubmedcentral proquest pubmed webofscience crossref rsc |
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| StartPage | 13426 |
| SubjectTerms | Amides Atomic energy levels Chemistry Chemistry, Multidisciplinary Chromophores Covalent bonds Electron paramagnetic resonance Electron spin Electrons Hexanes Physical Sciences Rhodamine Science & Technology Separation Spectra Time dependence Toluene |
| Title | A long-lived charge-separated state of spiro compact electron donor-acceptor dyads based on rhodamine and naphthalenediimide chromophores |
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