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Polymers 2018, 10(6), 654; https://doi.org/10.3390/polym10060654

Free-Radical Copolymerization of Dibenzofulvene with (Meth)acrylates Leading to π-Stacked Copolymers

1
Institute for Catalysis (ICAT) and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N 21, W 10, Kita-ku, Sapporo 001-0021, Japan
2
Integrated Research Consortium on Chemical Sciences (IRCCS), Institute for Catalysis (ICAT), Hokkaido University, N21 W10, Kita-ku, Sapporo 001-0021, Japan
*
Author to whom correspondence should be addressed.
Received: 28 May 2018 / Revised: 6 June 2018 / Accepted: 9 June 2018 / Published: 11 June 2018
(This article belongs to the Special Issue π-Stacked Polymers)
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Abstract

Copolymerizations of dibenzofulvene (DBF) with methyl methacrylate (MMA), 2-hydroxyethyl methacrylate (HEMA), methyl acrylate (MA), and 2-hydroxyethyl acrylate (HEA) were conducted under free radical conditions in toluene using α,α′-azobisisobutylonitrile (AIBN) as the initiator. In the copolymerizations, DBF indicated much higher reactivity than the comonomers, and the products comprised mainly of DBF units. NMR, UV, and fluorescence spectra, as well as electrochemical features indicated that the copolymers possess both isolated and rather short, sequential (meth)acrylate units, as well as π-stacked and unstacked DBF sequences. Isolated (meth)acrylate units are proposed to be sandwiched between DBF units. The ratios of π-stacked and unstacked side-chain fluorene groups of DBF units in excited states were accurately determined on the basis of fluorescent emission spectra; DBF units are mostly π-stacked in excited states as disclosed by fluorescence spectra. Two types of π-stacked sequences were suggested to be present in the ground state by electrochemical analysis. The copolymers exhibited higher solubility than pure poly(DBF). View Full-Text
Keywords: π-stacked polymer; dibenzofulvene; conformation; methacrylate; acrylate; radical polymerization; fluorescence; excimer; cyclic voltammetry π-stacked polymer; dibenzofulvene; conformation; methacrylate; acrylate; radical polymerization; fluorescence; excimer; cyclic voltammetry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Luo, J.; Wang, Y.; Nakano, T. Free-Radical Copolymerization of Dibenzofulvene with (Meth)acrylates Leading to π-Stacked Copolymers. Polymers 2018, 10, 654.

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