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Bent naphthodithiophenes: synthesis and characterization of isomeric fluorophores
Thiophene-containing heteroarenes are one of the most well-known classes of π-conjugated building blocks for photoactive molecules. Isomeric naphthodithiophenes (NDTs) are at the forefront of this research area due to their straightforward synthesis and derivatization. Notably, NDT geometries that a...
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Published in: | RSC advances 2024-08, Vol.14 (35), p.2512-25129 |
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Main Authors: | , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites |
Online Access: | Get full text |
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Summary: | Thiophene-containing heteroarenes are one of the most well-known classes of π-conjugated building blocks for photoactive molecules. Isomeric naphthodithiophenes (NDTs) are at the forefront of this research area due to their straightforward synthesis and derivatization. Notably, NDT geometries that are bent - such as naphtho[2,1-
b
:3,4-
b
′]dithiophene (α-NDT) and naphtho[1,2-
b
:4,3-
b
′]dithiophene (β-NDT) - are seldom employed as photoactive small molecules. This report investigates how remote substituents impact the photophysical properties of isomeric α- and β-NDTs. The orientation of the thiophene units plays a critical role in the emission: in the
α(OHex)R
2
series conjugation from the end-caps to the NDT core is apparent, while in the
β(O
i
-Pent)R
2
series minimal change is observed unless strong electron acceptors, such as
β(O
i
-Pent)(PhCF
3
)
2
, are employed. This push-pull acceptor-donor-acceptor (A-D-A) fluorophore exhibits positive fluorosolvatochromism that correlates with increasing solvent polarity parameter,
E
T
(30). In total, these results highlight how remote substituents are able to modulate the emission of isomeric bent NDTs.
Isomeric bent naphthodithiophene fluorophores: so you are telling me there is a difference? Probing bent naphthodithiophene-centered fluorophores photophysical response to remote substituents. |
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ISSN: | 2046-2069 2046-2069 |
DOI: | 10.1039/d4ra04850d |