Spin–Vibronic Control of Intersystem Crossing in Iodine-Substituted Heptamethine Cyanines
Spin–orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming recognized as an important mechanism for controlling the course of photochemical reactions. Here, we show that the involvement of spin–vibronic co...
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| Published in | Journal of organic chemistry Vol. 88; no. 11; pp. 6716 - 6728 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
02.06.2023
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-3263 1520-6904 1520-6904 |
| DOI | 10.1021/acs.joc.3c00005 |
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| Abstract | Spin–orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming recognized as an important mechanism for controlling the course of photochemical reactions. Here, we show that the involvement of spin–vibronic coupling is essential for understanding the photophysics and photochemistry of heptamethine cyanines (Cy7), bearing iodine as a heavy atom in the C3′ position of the chain and/or a 3H-indolium core, as potential triplet sensitizers and singlet oxygen producers in methanol and aqueous solutions. The sensitization efficiency was found to be an order of magnitude higher for the chain-substituted than the 3H-indolium core-substituted derivatives. Our ab initio calculations demonstrate that while all optimal structures of Cy7 are characterized by negligible spin–orbit coupling (tenths of cm–1) with no dependence on the position of the substituent, molecular vibrations lead to its significant increase (tens of cm–1 for the chain-substituted cyanines), which allowed us to interpret the observed position dependence. |
|---|---|
| AbstractList | Spin–orbit coupling between electronic states
of different
multiplicity can be strongly coupled to molecular vibrations, and
this interaction is becoming recognized as an important mechanism
for controlling the course of photochemical reactions. Here, we show
that the involvement of spin–vibronic coupling is essential
for understanding the photophysics and photochemistry of heptamethine
cyanines (Cy7), bearing iodine as a heavy atom in the C3′ position
of the chain and/or a 3H-indolium core, as potential
triplet sensitizers and singlet oxygen producers in methanol and aqueous
solutions. The sensitization efficiency was found to be an order of
magnitude higher for the chain-substituted than the 3H-indolium core-substituted derivatives. Our ab initio calculations
demonstrate that while all optimal structures of Cy7 are characterized
by negligible spin–orbit coupling (tenths of cm–1) with no dependence on the position of the substituent, molecular
vibrations lead to its significant increase (tens of cm–1 for the chain-substituted cyanines), which allowed us to interpret
the observed position dependence. Spin-orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming recognized as an important mechanism for controlling the course of photochemical reactions. Here, we show that the involvement of spin-vibronic coupling is essential for understanding the photophysics and photochemistry of heptamethine cyanines (Cy7), bearing iodine as a heavy atom in the C3' position of the chain and/or a 3H-indolium core, as potential triplet sensitizers and singlet oxygen producers in methanol and aqueous solutions. The sensitization efficiency was found to be an order of magnitude higher for the chain-substituted than the 3H-indolium core-substituted derivatives. Our ab initio calculations demonstrate that while all optimal structures of Cy7 are characterized by negligible spin-orbit coupling (tenths of cm-¹) with no dependence on the position of the substituent, molecular vibrations lead to its significant increase (tens of cm-¹ for the chain-substituted cyanines), which allowed us to interpret the observed position dependence. Spin-orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming recognized as an important mechanism for controlling the course of photochemical reactions. Here, we show that the involvement of spin-vibronic coupling is essential for understanding the photophysics and photochemistry of heptamethine cyanines (Cy7), bearing iodine as a heavy atom in the C3 ' position of the chain and/or a 3H-indolium core, as potential triplet sensitizers and singlet oxygen producers in methanol and aqueous solutions. The sensitization efficiency was found to be an order of magnitude higher for the chain substituted than the 3H-indolium core-substituted derivatives. Our ab initio calculations demonstrate that while all optimal structures of Cy7 are characterized by negligible spin-orbit coupling (tenths of cm(-1)) with no dependence on the position of the substituent, molecular vibrations lead to its significant increase (tens of cm(-1) for the chain-substituted cyanines), which allowed us to interpret the observed position dependence. Spin-orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming recognized as an important mechanism for controlling the course of photochemical reactions. Here, we show that the involvement of spin-vibronic coupling is essential for understanding the photophysics and photochemistry of heptamethine cyanines (Cy7), bearing iodine as a heavy atom in the C3' position of the chain and/or a 3 -indolium core, as potential triplet sensitizers and singlet oxygen producers in methanol and aqueous solutions. The sensitization efficiency was found to be an order of magnitude higher for the chain-substituted than the 3 -indolium core-substituted derivatives. Our ab initio calculations demonstrate that while all optimal structures of Cy7 are characterized by negligible spin-orbit coupling (tenths of cm ) with no dependence on the position of the substituent, molecular vibrations lead to its significant increase (tens of cm for the chain-substituted cyanines), which allowed us to interpret the observed position dependence. Spin-orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming recognized as an important mechanism for controlling the course of photochemical reactions. Here, we show that the involvement of spin-vibronic coupling is essential for understanding the photophysics and photochemistry of heptamethine cyanines (Cy7), bearing iodine as a heavy atom in the C3' position of the chain and/or a 3H-indolium core, as potential triplet sensitizers and singlet oxygen producers in methanol and aqueous solutions. The sensitization efficiency was found to be an order of magnitude higher for the chain-substituted than the 3H-indolium core-substituted derivatives. Our ab initio calculations demonstrate that while all optimal structures of Cy7 are characterized by negligible spin-orbit coupling (tenths of cm-1) with no dependence on the position of the substituent, molecular vibrations lead to its significant increase (tens of cm-1 for the chain-substituted cyanines), which allowed us to interpret the observed position dependence.Spin-orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming recognized as an important mechanism for controlling the course of photochemical reactions. Here, we show that the involvement of spin-vibronic coupling is essential for understanding the photophysics and photochemistry of heptamethine cyanines (Cy7), bearing iodine as a heavy atom in the C3' position of the chain and/or a 3H-indolium core, as potential triplet sensitizers and singlet oxygen producers in methanol and aqueous solutions. The sensitization efficiency was found to be an order of magnitude higher for the chain-substituted than the 3H-indolium core-substituted derivatives. Our ab initio calculations demonstrate that while all optimal structures of Cy7 are characterized by negligible spin-orbit coupling (tenths of cm-1) with no dependence on the position of the substituent, molecular vibrations lead to its significant increase (tens of cm-1 for the chain-substituted cyanines), which allowed us to interpret the observed position dependence. |
| Author | Slavíček, Petr Tovtik, Radek Klán, Petr Štacková, Lenka Muchová, Eva |
| AuthorAffiliation | Department of Chemistry, Faculty of Science RECETOX, Faculty of Science Department of Physical Chemistry |
| AuthorAffiliation_xml | – name: Department of Physical Chemistry – name: Department of Chemistry, Faculty of Science – name: RECETOX, Faculty of Science |
| Author_xml | – sequence: 1 givenname: Radek surname: Tovtik fullname: Tovtik, Radek organization: RECETOX, Faculty of Science – sequence: 2 givenname: Eva surname: Muchová fullname: Muchová, Eva organization: Department of Physical Chemistry – sequence: 3 givenname: Lenka surname: Štacková fullname: Štacková, Lenka organization: RECETOX, Faculty of Science – sequence: 4 givenname: Petr orcidid: 0000-0002-5358-5538 surname: Slavíček fullname: Slavíček, Petr email: Petr.Slavicek@vscht.cz organization: Department of Physical Chemistry – sequence: 5 givenname: Petr orcidid: 0000-0001-6287-2742 surname: Klán fullname: Klán, Petr email: klan@sci.muni.cz organization: RECETOX, Faculty of Science |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37146036$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1002_chem_202402514 crossref_primary_10_1039_D3CS00585B crossref_primary_10_1002_chem_202303154 crossref_primary_10_1002_tcr_202400183 crossref_primary_10_1039_D4TB00535J crossref_primary_10_1039_D3CC05153F crossref_primary_10_1016_j_saa_2024_125540 crossref_primary_10_1016_j_dyepig_2024_112548 |
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| Snippet | Spin–orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming... Spin-orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming... Spin–orbit coupling between electronic states of different multiplicity can be strongly coupled to molecular vibrations, and this interaction is becoming... |
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| SubjectTerms | Chemistry Chemistry, Organic iodine methanol organic chemistry photochemistry Physical Sciences Science & Technology singlet oxygen |
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| Title | Spin–Vibronic Control of Intersystem Crossing in Iodine-Substituted Heptamethine Cyanines |
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