Phenyl-Substituted Cibalackrot Derivatives: Synthesis, Structure, and Solution Photophysics

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F23%3A00573362" target="_blank" >RIV/61388955:_____/23:00573362 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/23:00573362 RIV/60461373:22340/23:43926409
Result on the web
<a href="https://doi.org/10.1021/acs.joc.2c02706" target="_blank" >https://doi.org/10.1021/acs.joc.2c02706</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.2c02706" target="_blank" >10.1021/acs.joc.2c02706</a>

Result language
angličtina
Original language name
Phenyl-Substituted Cibalackrot Derivatives: Synthesis, Structure, and Solution Photophysics
Original language description
Three symmetrically and three unsymmetrically substituted cibalackrot (7,14-diphenyldiindolo[3,2,1-de:3′,2′,1′-ij][1,5]naphthyridine-6,13-dione, 1) dyes carrying two derivatized phenyl rings have been synthesized as candidates for molecular electronics and especially for singlet fission, a process of interest for solar energy conversion. Solution measurements provided singlet and triplet excitation energies and fluorescence yields and lifetimes, conformational properties were analyzed computationally. The molecular properties are close to ideal for singlet fission. However, crystal structures, obtained by single-crystal X-ray diffraction (XRD), are rather similar to those of the polymorphs of solid 1, in which the formation of a charge-separated state followed by intersystem crossing, complemented with excimer formation, outcompetes singlet fission. Results of calculations by the approximate SIMPLE method suggest which ones among the solid derivatives are the best candidates for singlet fission, but it appears difficult to change the crystal packing in a desirable direction. We also describe the preparation of three specifically deuteriated versions of 1, expected to help sort out the mechanism of fast intersystem crossing in its charge-separated state.
Czech name
—
Czech description
—

Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10403 - Physical chemistry

Project
<a href="/en/project/GA19-22806S" target="_blank" >GA19-22806S: Singlet Fission: Redox and Photophysics of Captodative Biradicaloids</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)