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Soluble Adamantyl‐Substituted Oligothiophenes with Short Fluorescence Decay: An Approach for Ultrafast Optical Signal Processing
Author(s) -
Schlücker Thorben,
Dhayalan Vasudevan,
Langhals Heinz,
Sämann Christoph,
Knochel Paul
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500150
Subject(s) - chemistry , terthiophene , fluorescence , oligomer , quantum yield , photochemistry , negishi coupling , stokes shift , polymer chemistry , molecule , organic chemistry , physics , quantum mechanics , catalysis
Abstract THF‐soluble, adamantyl‐substituted oligothiophenes ( n =1–3) were prepared via Negishi cross‐coupling reactions. Thus, the synthesis of 2‐(1‐adamantyl)quaterthiophene was realized by cross‐coupling of 5‐bromo‐2′′‐(1‐adamantyl)terthiophene with 2‐thienylzinc chloride. Treatment of these oligothiophenes with FeCl 3 affords the corresponding dimeric compounds, which have pigment properties. In contrast, the mono‐substituted (1‐adamantyl)oligothiophenes ( n =1–4) are readily soluble in organic solvents. Particularly the quarter‐oligomer displays remarkable optical properties such as an increased Stokes’ shift in combination with a very fast fluorescence decay of 0.39 ns and a high fluorescence quantum yield. The compound was incorporated in a solid poly(methyl methacrylate) matrix and its optical properties were nearly unaltered. This may allow applications in high‐throughput optical signal processing exceeding the GBit scale.