Synthesis of Viologens with Extended π−Conjugation and Their Photochromic Behavior on Near-IR Absorption

Nanasawa, Masato; Miwa, Makio; Hirai, Michiko; Kuwabara, Tetsuo

doi:10.1021/jo990911v

Cited by 72 publications

(41 citation statements)

References 15 publications

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“…我们还发现带有羟基的客体 5 也可以与大三环主体 1 形成超分子聚准[3]轮烷(1•5) n (图 S44) [13] , 络合模式与向大环的冠醚空腔(图 S45) [13] , 这种络合模式与大三环 [13] , 这与溶液中结果是一致的. 4 实验部分主体 1 [14] 与客体 3 [15] 、4 [16] 、6 [11] 以及(E)-1,2-二(4-吡啶基)乙烯 [17] , 1,4-二(吡啶-4-基)苯 [18] 按照文献方法合成. H 4.47, N 4.14; found C 39.15, H 4.11, N 4.15. …”

Section: 主体unclassified

Complexation of Triptycene-Derived Macrotricyclic Host with π-Extended Viologens

Han¹,

Zheng²,

Chen³

2015

Acta Chim. Sinica

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Development of novel macrocyclic hosts with the capability of binding selected substrates in specific complexation modes is always a very important and attractive topic in host-guest chemistry. Recently, we reported a novel macrotricyclic polyether containing two triptycene skeletons with rigid structure and two dibenzo-30-crown-10 moieties, which could show wide complexation abilities toward different kinds of guests. It was found that depending on the guests with different terminal functional groups and structures, the macrotricyclic polyether could form 1∶1 or 1∶2 complexes with the guests in different complexation modes in solution and also in the solid state. Moreover, the conformation of the macrocycle could easily be adjusted by the different encapsulated guests, which was to some extent similar to substrate induced fit of enzymes. It was also known that viologens with reversible single electron-accepting ability were usually used for the basic study of electrochemical and photoelectrochemical processes. They have also been widely utilized as electron deficient guests for host-guest chemistry. Compared with the viologens, π-extended viologens with conjugated structures have much more rich redox behaviors, and they could be used for photolithography, a source of electric oscillations, molecular electronic devices, and also as agents for charge transport across vesicles. However, the applications of π-extended viologens as guests in host-guest chemistry are still very limited. In this paper, complexation between the triptycene-derived macrotricyclic host and π-extended viologens in both solution and solid state was investigated in detail. It was found that depending on the guests with different linker-species and terminal functional groups, the macrotricyclic host could form 1∶1 or 1∶2 complexes with the guests in solution. Besides the 1∶1 or 1∶2 complexes, the macrotricyclic host could also form supramolecular poly [3]pseudorotaxane-type complexes with the guests in different complexation modes in the solid state. Formation of the complexes was proved by the 1 H NMR, ESI-MS spectra, and X-ray crystal structures.

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Section: 主体unclassified

Complexation of Triptycene-Derived Macrotricyclic Host with π-Extended Viologens

Han¹,

Zheng²,

Chen³

2015

Acta Chim. Sinica

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“…The diquaternary salt 1 was prepared by the reaction of 1,1Ј-bis(2,4-dinitrophenyl)-4,4Ј-bipyridinium dichloride [31] with an excess (2.3 equiv.) of 4-aminobenzyl alcohol by the Zincke reaction.…”

Section: Synthesismentioning

confidence: 99%

Triply Branched Viologen Stars: Synthesis and Polymerization by Peripheral Benzyl Coupling

2012

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The synthesis of 0 th (n = 1) and 1 st (n = 2) generation, monodisperse, star-shaped oligoviologens, C[(BnV ++ -PhV ++ ) n -CH 2 X] 3 , which consist of a phenyl or a 2,4,6-trimethylphenyl core (C) with triple 1,3,5-branches, in which each branch consists of a linear alternating series of diphenyl-(PhV ++ ) and dibenzyl viologens (BnV ++ ) and a variety of peripheral groups X (CH 3 , OH, Br), is described. According to MM+ modeling, the stars adopt a flat structure with the branches pointing towards the corners of an equilateral triangle with a centre-corner distances of 2.9 (n = 1) and 5.8 nm (n = 2, repulsive charge interaction). Discrete redox chemistry from the benzyl-(-0.27, -0.70 V) and phenyl viologen subunits (-0.12, -0.42 V vs. Ag/AgCl) is observed as a set of four interdigitated reduction waves, which involve 3 ϫ 4 = 12 (0 th generation) and 3 ϫ 8 = 24 electrons (1 st generation) as shown by

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“…N-hexyl-N 0 -(4-vinylbenzyl)-4,4 0 -bipyridinium bromide chloride was synthesized according to the method reported in the literature [20][21][22]. A mixed solution of 4,4 0 -bipyridine and hexylbromide (molar ratio 1.5:1) was heated at reflux in acetone for 24 h. The precipitate was washed with acetone, ether and then recrystallized from acetone.…”

Section: Synthesis Of Viologenmentioning

confidence: 99%

“…After the irradiation period, the film is exposed to air and allowed to bleach in the dark. In the presence of air, the reaction of the viologen radical cations with O 2 regenerates the viologen dication and this reaction has been known to be particularly fast because of the strong reductive ability of the viologen radical cation [12,21]. This results in the decrease of the intensities of the absorption bands at 615 and 407 nm.…”

Section: Graft Copolymerization Of Pet Films With Hvvmentioning

confidence: 99%

Antibacterial activity of polymeric substrate with surface grafted viologen moieties

2005

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Synthesis of Viologens with Extended π−Conjugation and Their Photochromic Behavior on Near-IR Absorption

Cited by 72 publications

References 15 publications

Complexation of Triptycene-Derived Macrotricyclic Host with π-Extended Viologens

Complexation of Triptycene-Derived Macrotricyclic Host with π-Extended Viologens

Triply Branched Viologen Stars: Synthesis and Polymerization by Peripheral Benzyl Coupling

Antibacterial activity of polymeric substrate with surface grafted viologen moieties

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