ChemInform Abstract: Synthesis of Some 1,8‐Naphthalic Anhydride Derivatives as Dyes for Polymeric Materials.

Grabtchev, I.; Philipova, T.

doi:10.1002/chin.199734175

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“…The luminescent properties of 1,8‐naphthalimides depend mainly on the polarization of the molecule due to the donor–acceptor interaction between the substituent in position C4 and the carbonyl groups in the imide part of the molecule . The relation between the structure of 1,8‐naphthalimides and their emission properties is known in considerable detail . Because of the wide properties tunability the 1,8‐naphthalimide luminophores are suitable for use (i) in the field of electronics and laser techniques, (ii) as dichroic dyes in liquid‐crystalline systems of the host–guest type, or (iii) as sensing materials and markers in medicine .…”

Section: Introductionmentioning

confidence: 99%

Copolymerization of N -(prop-1-yne-3-yl)-4-(piperidine-1-yl)-1,8-naphthalimide with Arylacetylenes into Fluorescent Polyacetylene-Type Conjugated Polymers

Sivkova

Trhlíková

Zednı́k

et al. 2015

Macromol. Chem. Phys.

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N -(prop-1-yne-3-yl)-4-(piperidine-1-yl)-1,8-naphthalimide (PNPr), i.e., the monomer with a terminal ethynyl group and 1,8-naphthalimide fl uorophore, has been successfully copolymerized with a series of monoethynylarenes into well-soluble high-molecular-weight ( M w up to 210 000) linear polyacetylene-type copolymers containing from 14 to 51 mol% units derived from PNPr. The copolymerization of PNPr with bifunctional 4,4′-diethynylbiphenyl provides polyacetylene-type micro/mesoporous fl uorescent network containing 8 mol% PNPr units and exhibiting the Brunauer-Emmett-Teller surface of ≈1000 m 2 g −1 . The copolymerizations (catalyzed with acetylacetonato(norborna-2,5-diene)rhodium complex, [Rh(nbd)acac]) proceed smoothly despite the fact that the homopolymerization of PNPr fails. The fl uorescence of PNPr (emission at ≈ 510 nm) has been retained after the incorporation of PNPr into the copolymers. The fl uorescence of the copolymers can be induced by a direct excitation of PNPr units or via an energy transfer mechanism. In the latter case, the comonomeric units with aromatic hydrocarbon fl uorophores (e.g., of the biphenyl-type) emitting at 380-400 nm (after irradiation with 300 nm UV radiation) serve as energy donors for fl uorescent PNPr acceptors. The difference between the wavelengths of the primary absorbed radiation and the fi nally emitted radiation is 210 nm.

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