Synthesis and Chemical Properties of Diacetylenes with Pyridinium and 4,4′-Bipyridinium Groups
Diacetylenes (DAs) having a dipolar D‐π‐A structure (D=donor: amino group; π=π‐conjugation core; A=acceptor: pyridinium (Py) and bipyridinium (BPy) groups), i.e., 4 (APBPyDA) and 5 (APPyPyDA), or an A‐π‐A structure, i.e., 7 (DBPyDA) and 8 (PyDA(Cl)), were obtained by 1 : 1 and 1 : 2 reactions of 4,4...
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| Published in | Helvetica chimica acta Vol. 93; no. 5; pp. 819 - 828 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Zürich
WILEY-VCH Verlag
01.05.2010
WILEY‐VCH Verlag Wiley |
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| Online Access | Get full text |
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| Abstract | Diacetylenes (DAs) having a dipolar D‐π‐A structure (D=donor: amino group; π=π‐conjugation core; A=acceptor: pyridinium (Py) and bipyridinium (BPy) groups), i.e., 4 (APBPyDA) and 5 (APPyPyDA), or an A‐π‐A structure, i.e., 7 (DBPyDA) and 8 (PyDA(Cl)), were obtained by 1 : 1 and 1 : 2 reactions of 4,4′‐(buta‐1,3‐diyne‐1,4‐diyl)bis[benzenamine] (APDA; 3) with 1‐(2,4‐dinitrophenyl)‐1′‐hexyl‐4,4′‐bipyridinium bromide chloride (1 : 1 : 1) (1), 1‐(2,4‐dinitrophenyl)‐4‐(pyridin‐4‐yl)pyridinium chloride (2), or 1‐(2,4‐dinitrophenyl)pyridinium chloride (6) (Schemes 1 and 2). The anion‐exchange reactions of 8 with NaI and Li(TCNQ) (TCNQ−=2,2′‐(cyclohexa‐2,5‐diene‐1,4‐diylidene)bis[propanedinitrile] radical ion (1−)) yielded the corresponding I− and TCNQ− salts 9 (PyDA(I)) and 10 (PyDA(TCNQ)). Compounds 10 and 4 exhibited a UV/VIS absorption due to a charge transfer between the TCNQ− and the pyridinium groups and a strong solute–solvent interaction of a dipolar solute molecule in the polar environment, respectively. Compounds 8–10 exhibited photoluminescence in solution, whereas 4 and 7 did not because of the presence of the 4,4′‐bipyridinium quenching groups. Differential‐scanning‐calorimetry (DSC) measurements suggested that the DAs obtained in this study can be converted into poly(diacetylenes) by thermal polymerization. |
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| AbstractList | Diacetylenes (DAs) having a dipolar D‐
π
‐A structure (D=donor: amino group;
π
=
π
‐conjugation core; A=acceptor: pyridinium (Py) and bipyridinium (BPy) groups),
i.e.
,
4
(APBPyDA) and
5
(APPyPyDA), or an A‐
π
‐A structure,
i.e.
,
7
(DBPyDA) and
8
(PyDA(Cl)), were obtained by 1 : 1 and 1 : 2 reactions of 4,4′‐(buta‐1,3‐diyne‐1,4‐diyl)bis[benzenamine] (APDA;
3
) with 1‐(2,4‐dinitrophenyl)‐1′‐hexyl‐4,4′‐bipyridinium bromide chloride (1 : 1 : 1) (
1
), 1‐(2,4‐dinitrophenyl)‐4‐(pyridin‐4‐yl)pyridinium chloride (
2
), or 1‐(2,4‐dinitrophenyl)pyridinium chloride (
6
) (
Schemes 1
and
2
). The anion‐exchange reactions of
8
with NaI and Li(TCNQ) (TCNQ
−
=2,2′‐(cyclohexa‐2,5‐diene‐1,4‐diylidene)bis[propanedinitrile] radical ion (1−)) yielded the corresponding I
−
and TCNQ
−
salts
9
(PyDA(I)) and
10
(PyDA(TCNQ)). Compounds
10
and
4
exhibited a UV/VIS absorption due to a charge transfer between the TCNQ
−
and the pyridinium groups and a strong solute–solvent interaction of a dipolar solute molecule in the polar environment, respectively. Compounds
8
–
10
exhibited photoluminescence in solution, whereas
4
and
7
did not because of the presence of the 4,4′‐bipyridinium quenching groups. Differential‐scanning‐calorimetry (DSC) measurements suggested that the DAs obtained in this study can be converted into poly(diacetylenes) by thermal polymerization. Diacetylenes (DAs) having a dipolar D-pi-A structure (D = donor: amino group;pi = pi-conjugation core; A = acceptor: pyridinium (Py) and bipyridinium (BPy) groups), i.e., 4 (APBPyDA) and 5 (APPyPyDA), or an A-pi-A structure, i.e., 7 (DBPyDA) and 8 (PyDA(Cl)), were obtained by 1: 1 and 1:2 reactions of 4,4'-(buta-1,3-diyne-1,4-diyl)bis[benzenamine] (APDA; 3) with 1-(2,4-dinitrophenyl)1'-hexy1-4,4'-bipyridinium bromide chloride (1 :1 :1) (1), 1-(2,4-dinitrophenyl)-4-(pyridin-4-yl)pyridinium chloride (2), or 1-(2,4-dinitrophenyl)pyridinium chloride (6) (Schemes 1 and 2). The anion-exchange reactions of 8 with NaI and Li(TCNQ) (TCNQ(-) = 2,2'-(cyclohexa-2,5-diene-1,4-diylidene)bis[propanedinitrile] radical ion (1-)) yielded the corresponding I- and TCNQ(-) salts 9 (PyDA(I)) and 10 (PyDA(TCNQ)). Compounds 10 and 4 exhibited a UV/VIS absorption due to a charge transfer between the TCNQ(-) and the pyridinium groups and a strong solute solvent interaction of a dipolar solute molecule in the polar environment, respectively. Compounds 8-10 exhibited photoluminescence in solution, whereas 4 and 7 did not because of the presence of the 4,4'-bipyridinium quenching groups. Differential-scanning-calorimetry (DSC) measurements suggested that the DAs obtained in this study can be converted into poly(diacetylenes) by thermal polymerization. Diacetylenes (DAs) having a dipolar D‐π‐A structure (D=donor: amino group; π=π‐conjugation core; A=acceptor: pyridinium (Py) and bipyridinium (BPy) groups), i.e., 4 (APBPyDA) and 5 (APPyPyDA), or an A‐π‐A structure, i.e., 7 (DBPyDA) and 8 (PyDA(Cl)), were obtained by 1 : 1 and 1 : 2 reactions of 4,4′‐(buta‐1,3‐diyne‐1,4‐diyl)bis[benzenamine] (APDA; 3) with 1‐(2,4‐dinitrophenyl)‐1′‐hexyl‐4,4′‐bipyridinium bromide chloride (1 : 1 : 1) (1), 1‐(2,4‐dinitrophenyl)‐4‐(pyridin‐4‐yl)pyridinium chloride (2), or 1‐(2,4‐dinitrophenyl)pyridinium chloride (6) (Schemes 1 and 2). The anion‐exchange reactions of 8 with NaI and Li(TCNQ) (TCNQ−=2,2′‐(cyclohexa‐2,5‐diene‐1,4‐diylidene)bis[propanedinitrile] radical ion (1−)) yielded the corresponding I− and TCNQ− salts 9 (PyDA(I)) and 10 (PyDA(TCNQ)). Compounds 10 and 4 exhibited a UV/VIS absorption due to a charge transfer between the TCNQ− and the pyridinium groups and a strong solute–solvent interaction of a dipolar solute molecule in the polar environment, respectively. Compounds 8–10 exhibited photoluminescence in solution, whereas 4 and 7 did not because of the presence of the 4,4′‐bipyridinium quenching groups. Differential‐scanning‐calorimetry (DSC) measurements suggested that the DAs obtained in this study can be converted into poly(diacetylenes) by thermal polymerization. |
| Author | Sato, Moriyuki Kimura, Shunsuke Higashi, Hideo Yamaguchi, Isao |
| Author_xml | – sequence: 1 givenname: Isao surname: Yamaguchi fullname: Yamaguchi, Isao email: iyamaguchi@riko.shimane-u.ac.jp organization: Department of Material Science, Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan (phone: +81-852-326421) – sequence: 2 givenname: Hideo surname: Higashi fullname: Higashi, Hideo organization: Department of Material Science, Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan (phone: +81-852-326421) – sequence: 3 givenname: Shunsuke surname: Kimura fullname: Kimura, Shunsuke organization: Department of Material Science, Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan (phone: +81-852-326421) – sequence: 4 givenname: Moriyuki surname: Sato fullname: Sato, Moriyuki organization: Department of Material Science, Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan (phone: +81-852-326421) |
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| Snippet | Diacetylenes (DAs) having a dipolar D‐π‐A structure (D=donor: amino group; π=π‐conjugation core; A=acceptor: pyridinium (Py) and bipyridinium (BPy) groups),... Diacetylenes (DAs) having a dipolar D‐ π ‐A structure (D=donor: amino group; π = π ‐conjugation core; A=acceptor: pyridinium (Py) and bipyridinium (BPy)... Diacetylenes (DAs) having a dipolar D-pi-A structure (D = donor: amino group;pi = pi-conjugation core; A = acceptor: pyridinium (Py) and bipyridinium (BPy)... |
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| SubjectTerms | 4,4′‐Bipyridine 4′-Bipyridine Anion-exchange reactions Chemistry Chemistry, Multidisciplinary Diacetylenes Photoluminescence Physical Sciences Polymerization Pyridinium salts Science & Technology Viologen |
| Title | Synthesis and Chemical Properties of Diacetylenes with Pyridinium and 4,4′-Bipyridinium Groups |
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