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Blue Emitting 3 π–2 Spiro Terfluorene–Indenofluorene Isomers: A Structure–Properties Relationship Study
Author(s) -
Poriel Cyril,
RaultBerthelot Joëlle,
Thirion Damien,
Barrière Frédéric,
Vignau Laurence
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102212
Subject(s) - fluorene , intramolecular force , oled , chemistry , molecule , organic electronics , fluorescence , photochemistry , materials science , stereochemistry , layer (electronics) , polymer , organic chemistry , physics , optics , transistor , voltage , quantum mechanics
Two novel terfluorenyl derivatives, 2,2′′,7,7′′‐tetrakis(9,9‐dioctyl‐9 H ‐fluoren‐2‐yl)dispiro[fluorene‐9,11′‐indeno‐(2,1‐ a )‐fluorene‐12′,9′′‐fluorene] ((2,1‐ a )‐DST‐IF) and 2,2′′,7,7′′‐tetrakis(9,9‐dioctyl‐9 H ‐fluoren‐2‐yl)dispiro‐ [fluorene‐9,6′‐indeno‐(1,2‐ b )‐fluorene‐12′,9′′‐fluorene] ((1,2‐ b )‐DST‐IF) have been synthesized by two different synthetic approaches. These terfluorenyl derivatives possess a different central indenofluorene core, namely (2,1‐ a )‐indenofluorene or (1,2‐ b )‐indenofluorene, which imposes two distinct geometry profiles, and different structural environments for the terfluorenyl fluorophores that translates into drastically different optical and electrochemical properties for (2,1‐ a )‐DST‐IF and (1,2‐ b )‐DST‐IF. These properties have been carefully studied through a combined experimental and theoretical approach. The (2,1‐ a )‐DST‐IF isomer has been successfully used as emitting layer in a blue single‐layer small‐molecule organic light‐emitting diode (SMOLED) and appears as the first example of a blue emission arising from intramolecular terfluorenyl excimers. Regarding the importance of terfluorenyl derivatives in organic electronics, the present structure–properties relationship study, may open new avenues in the design of efficient blue fluorophores.