Acid-catalyzed brominations, deuterations, rearrangements, and debrominations of thiophenes under mild conditions

Kellogg, Richard M.; Schaap, A. Paul; Harper, Edwin T.; Wynbert, Hans

doi:10.1021/jo01271a064

Cited by 95 publications

(39 citation statements)

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“…Then TPZ was synthesized by a modified method of Ref. [21] to study the interaction of TPZ with metal ions. When Hg 2þ was added into TPZ solution in THF or CHCl 3 /DMSO (1:1 v/v), the similar absorption spectral change (i.e., main absorption peak weakened and a new absorption peak at longer wavelength appeared) took place (see Fig.…”

Section: Full Papermentioning

confidence: 99%

An Alternative Copolymer of Carbazole and Thieno[3,4b]‐Pyrazine: Synthesis and Mercury Detection

Zou

Wan

Sang

et al. 2008

Adv Funct Materials

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A donor‐π‐acceptor (D‐π‐A) alternative copolymer of carbazole and thieno[3,4b]‐pyrazine [P(CZ‐TPZ)] is synthesized through a Wittig–Horner reaction. In dilute THF solution, the absorption spectrum of P(CZ‐TPZ) shows two absorption peaks at 306 and 452 nm, respectively, and the PL spectrum of the polymer solution displays a PL peak maximum at 543 nm. The polymer possesses relatively high sensitivity and selectivity for Hg2+ detection. Upon addition of Hg2+ into its THF solution (containing 0.3% CH3CN), P(CZ‐TPZ) exhibits a new absorption peak at 560∼600 nm and its emission was quenched dramatically. The Hg2+ detection shows high selectivity in comparison with the other cations of Na+, K+, Mg2+, Ba2+, Al3+, Cu2+, Cd2+, Pb2+, Ni2+, Mn2+, and Co2+. The Hg2+ detection limit of the polymer solution by emission quenching is found to be 1 × 10−7 mol L−1. P(CZ‐TPZ) also shows a selective chromogenic behavior toward Hg2+ with color change of the solution from yellow to blue dark which can be detected with the naked eye, the detection limit reaches 1 × 10−6 mol L−1 with a 1 × 10−4 mol L−1 polymer solution. The absorption and PL spectral change can be resumed after adding thiourea, therefore the sensing ability of the polymer is re‐usable with the treatment of thiourea. The results indicate that P(CZ‐TPZ) is a promising chemosensor for the Hg2+ detection.

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Section: Full Papermentioning

confidence: 99%

An Alternative Copolymer of Carbazole and Thieno[3,4b]‐Pyrazine: Synthesis and Mercury Detection

Zou

Wan

Sang

et al. 2008

Adv Funct Materials

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“…In recent studies [19,20], similar alkyl-derivatized thiophenes were obtained by a two or even four step procedure that involved the acylation of the thiophene moiety and the subsequent reduction of the obtained ketone with BH 3 or N 2 H 4 (the latter requiring temporary replacement of the bromide with a hydroquinone ether). The alkylated thiophene derivative was then brominated in the free α-position using N-bromosuccinimide (NBS) in a mixture of acetic acid and chloroform [21] at room temperature and gave the regioselectively brominated thiophene derivative 3 (84-92% yield).…”

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confidence: 99%

A practical synthesis of functionalized alkyl‐oligothiophenes for molecular self‐assembly

Michalitsch

ElKassmi

Yassar

et al. 2001

Journal of Heterocyclic Chem

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A synthesis for oligothiophenes that carry an alkyl sidechain with a terminal thiol group is presented. The procedure consists of three basic steps and uses well-known and simple synthetic chemistry. Nevertheless, this strategy for preparing functionalized oligothiophenes provides overall yields that are as high as 25-30% and represents a convenient route towards this interesting class of materials.

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“…[9] 2,5-dibromo-3-hexyl-thiophene was prepared as described in the literature. [10] All reactions were carried out with oven-dried glassware and dry solvents in an argon atmosphere, unless otherwise stated. AIBN was purchased from Aldrich and recrystallized twice from methanol.…”

Section: Methodsmentioning

confidence: 99%

A Simple Route to Rod‐Coil Block Copolymers of Oligo‐ and Polythiophenes with PMMA and Polystyrene

Antoun¹,

Iraqi²,

Kergoat³

et al. 2011

Macro Chemistry & Physics

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A simple and efficient approach for the preparation of rod‐coil block copolymers comprising oligo‐ and polythiophenes blocks together with PMMA or PS blocks is described. The block copolymers were prepared using a two‐step procedure. α,ω‐dicarboxy‐terminated oligothiophenes and carboxy terminated poly(3‐hexylthiophene) were first prepared. These were then reacted with P4S10 in a second step to generate the α,ω‐thioester terminated oligothiophenes and poly(3‐hexylthiophene)s which were subsequently used in a one‐pot reaction as RAFT polymerization agents with methylmethacrylate and styrene. The di‐ and tri‐block copolymers hence obtained were fully characterized, both in solution and as thin films. magnified image

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Acid-catalyzed brominations, deuterations, rearrangements, and debrominations of thiophenes under mild conditions

Cited by 95 publications

References 0 publications

An Alternative Copolymer of Carbazole and Thieno[3,4b]‐Pyrazine: Synthesis and Mercury Detection

An Alternative Copolymer of Carbazole and Thieno[3,4b]‐Pyrazine: Synthesis and Mercury Detection

A practical synthesis of functionalized alkyl‐oligothiophenes for molecular self‐assembly

A Simple Route to Rod‐Coil Block Copolymers of Oligo‐ and Polythiophenes with PMMA and Polystyrene

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