Central Ring Puckering Enhances the Stokes Shift of Xanthene Dyes

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00583934" target="_blank" >RIV/61388963:_____/24:00583934 - isvavai.cz</a>
Alternative codes found
RIV/00216224:14310/24:00136181 RIV/00216208:11310/24:10481977
Result on the web
<a href="https://doi.org/10.1002/chem.202400024" target="_blank" >https://doi.org/10.1002/chem.202400024</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.202400024" target="_blank" >10.1002/chem.202400024</a>

Result language
angličtina
Original language name
Central Ring Puckering Enhances the Stokes Shift of Xanthene Dyes
Original language description
Small-molecule dyes are generally designed based on well-understood electronic effects. However, steric hindrance can promote excited-state geometric relaxation, increasing the difference between the positions of absorption and emission bands (the Stokes shift). Accordingly, we hypothesized that sterically induced central ring puckering in xanthene dyes could be used to systematically increase their Stokes shift. Through a combined experimental/quantum-chemical approach, we screened a group of (9-acylimino)-pyronin dyes with a perturbed central ring geometry. Our results showed that an atom with sp(3) hybridization in position 10 of (9-acylimino)-pyronins induces central ring puckering and facilitates excited-state geometric relaxation, thereby markedly enhancing their Stokes shifts (by up to similar to 2000 cm(-1)). Thus, we prepared fluorescent (9-acylimino)-pyronin pH sensors, which showed a Stokes shift disparity between acid and base forms of up to similar to 8700 cm(-1). Moreover, the concept of ring puckering-enhanced Stokes shift can be applied to a wide range of xanthene analogues found in the literature. Therefore, central ring puckering may be reliably used as a strategy for enhancing Stokes shifts in the rational design of dyes.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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