Synthesis and properties of a fluorene-capped isotruxene:: A new unsymmetrical star-shaped π-system

被引:45
作者
Yang, Jye-Shane [1 ]
Lee, Yar-Ru
Yan, Jyu-Lun
Lu, Ming-Chun
机构
[1] Natl Taiwan Univ, Dept Chem, Taipei 10617, Taiwan
[2] Natl Cent Univ, Dept Chem, Chungli 32054, Taiwan
关键词
D O I
10.1021/ol062408s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] An unsymmetrical star-shaped d-system (1) with an isotruxene core and three fluorene arms has been synthesized, and its photophysical, electrochemical, and thermochemical properties have been investigated and compared with the corresponding symmetrical truxene derivatives 2a-d (Kanibolotsky, A. L.; Berridge, R.; Skabara, P. J.; Perepichka, I. F.; Bradley, D. D. C.; Koeberg, M. J. Am. Chem. Soc. 2004, 126, 13695-13702). Stronger electronic couplings between the arms in 1 vs 2a-d lead to lower optical band gap, larger splitting in oxidation potentials, and superior thermostability.
引用
收藏
页码:5812 / 5816
页数:4
相关论文
共 46 条
[11]   Synthesis, characterization, and optical response of dipolar and non-dipolar poly(phenylenevinylene) dendrimers [J].
Díez-Barra, E ;
García-Martínez, JC ;
Merino, S ;
del Rey, R ;
Rodríguez-López, J ;
Sánchez-Verdú, P ;
Tejeda, J .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5664-5670
[12]   Nanosized π-conjugated molecules based on truxene and porphyrin:: Synthesis and high fluorescence quantum yields [J].
Duan, XF ;
Wang, JL ;
Pei, J .
ORGANIC LETTERS, 2005, 7 (19) :4071-4074
[13]   Meta-conjugation and excited-state coupling in phenylacetylene dendrimers [J].
Gaab, KM ;
Thompson, AL ;
Xu, JJ ;
Martínez, TJ ;
Bardeen, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9288-9289
[14]  
Halim M, 1999, ADV MATER, V11, P371, DOI 10.1002/(SICI)1521-4095(199903)11:5<371::AID-ADMA371>3.0.CO
[15]  
2-1
[16]   Origin of the broken conjugation in m-phenylene linked conjugated polymers [J].
Hong, SY ;
Kim, DY ;
Kim, CY ;
Hoffmann, R .
MACROMOLECULES, 2001, 34 (18) :6474-6481
[17]   Synthesis and properties of monodisperse oligofluorene-functionalized truxenes: Highly fluorescent star-shaped architectures [J].
Kanibolotsky, AL ;
Berridge, R ;
Skabara, PJ ;
Perepichka, IF ;
Bradley, DDC ;
Koeberg, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13695-13702
[18]   STRUCTURE AND OPTICAL-ABSORPTION OF OLIGO(P-PHENYLENEVINYLENE AND M-PHENYLENEVINYLENE) AND THEIR RADICAL-ANIONS - A COMPARATIVE THEORETICAL-STUDY [J].
KARABUNARLIEV, S ;
BAUMGARTEN, M ;
TYUTYULKOV, N ;
MULLEN, K .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (46) :11892-11901
[19]   SYNTHESIS AND NONLINEAR OPTICS OF SOLUBLE POLY(PHENYLENEETHYNYLENE) [J].
KONDO, K ;
OKUDA, M ;
FUJITANI, T .
MACROMOLECULES, 1993, 26 (26) :7382-7382
[20]   Spectroscopic evidence for excitonic localization in fractal antenna supermolecules [J].
Kopelman, R ;
Shortreed, M ;
Shi, ZY ;
Tan, WH ;
Xu, ZF ;
Moore, JS ;
BarHaim, A ;
Klafter, J .
PHYSICAL REVIEW LETTERS, 1997, 78 (07) :1239-1242