NDLI: Fluorescence of New o-Carborane Compounds with Different Fluorophores: Can it be Tuned?

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Fluorescence of New o-Carborane Compounds with Different Fluorophores: Can it be Tuned?

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Ferrer-ugalde, Albert González-campo, Arántzazu Viñas, Clara Teixidor, Francesc Farfán, Norberto Sousa-pedrares, Antonio Rodríguez-romero, Jesús Sillanpää, Reijo Núñez, Rosario Santillan, Rosa
Description	Author Affiliation: Ferrer-Ugalde A ( Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus U.A.B., 08193 Bellaterra, Barcelona (Spain).)
Abstract	Two sets of o-carborane derivatives incorporating fluorene and anthracene fragments as fluorophore groups have been successfully synthesized and characterized, and their photophysical properties studied. The first set, comprising fluorene-containing carboranes 6–9, was prepared by catalyzed hydrosilylation reactions of ethynylfluorene with appropriate carboranylsilanes. The compound 1-[(9,9-dioctyl-fluorene-2-yl)ethynyl]carborane (11) was synthesized by the reaction of 9,9-dioctyl-2-ethynylfluorene and decaborane $(B_{10}H_{14}).$ Furthermore, reactions of the lithium salt of 11 with 1 equivalent of 4-(chloromethyl)styrene or 9-(chloromethyl)anthracene yielded compounds 12 and 13. Members of the second set of derivatives, comprising anthracene-containing carboranes, were synthesized by reactions of monolithium or dilithium salts of $1-Me-1,2-C_{2}B_{10}H_{11},$ $1-Ph-1,2-C_{2}B_{10}H_{11},$ and $1,2-C_{2}B_{10}H_{12}$ with 1 or 2 equivalents of 9-(chloromethyl)anthracene, respectively, to produce compounds 14–16. In addition, 2 equivalents of the monolithium salts of $1-Me-1,2-C_{2}B_{10}H_{11}$ (Me-o-carborane) and $1-Ph-1,2-C_{2}B_{10}H_{11}$ (Ph-o-carborane) were reacted with 9,10-bis(chloromethyl)anthracene to produce compounds 17 and 18, respectively. Fluorene derivatives 6–9 exhibit moderate fluorescence quantum yields (32–44 %), whereas 11–13, in which the fluorophore is bonded to the $C_{cluster}$ $(C_{c}),$ show very low emission intensity (6 %) or complete fluorescence quenching. The anthracenyl derivatives containing the Me-o-carborane moiety exhibit notably high fluorescence emissions, with $ϕ_{F}=82$ and 94 %, whereas their Ph-o-carborane analogues are not fluorescent at all. For these compounds, we have observed a correlation between the $C_{c}C_{c}$ bond length and the fluorescence intensity in $CH_{2}Cl_{2}$ solution, comparable to that observed for previously reported styrene-containing carboranes. Thus, our hypothesis is that for systems of this type the fluorescence may be tuned and even predicted by changing the substituent on the adjacent $C_{c}.$
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	32
Volume Number	20
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2014-08-04
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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