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1 cm -1 = -1 cm -1
2
3
4 ( ) ( )
5 1) 2) ( ) (T c )
6
7 MI 100%( 90% )
8 ( T c 9 K) (T c 23 K) (T c 135 K) (T c 40 K) (T c 33 K) (T c 14 K)
9 BC - T c 30K BC - + T c
10 Little - T c 1000 K
11
12
13 酸化還元状態の制約 D 0 LUMO HOMO LUMO HOMO-LUMO D +1 D +2 D 0 D +0.5 D 0 D +1 D +1 D 0
14 D +0.5 D 0 D +1 D +1 D 0 D +0.5 D +1 D +1 D +2 D 0
15 多段階酸化還元系 -e -e e +e TTF TTF + TTF 2+ NC CN NC - CN NC - CN +e +e -e -e NC CN NC CN NC - CN TCNQ TCNQ - TCNQ 2-
16 分子の積層様式
17 D D + D A
18 有機導電体の歴史 NC CN -Br x (x = 3-4) perylene-br x (1954) NC CN TCNQ (1960) TTF (1970)
19 TTF TCNQ TTF NC NC TCNQ CN CN TTF TCNQ
20 TTF TCNQ の導電性 -
21
22 k F (p F ) ( E) T, E E k F (p F ) T, (T MI ) T MI
23 k y k y 2k F k x k x -k F k F -k F k F 2k F ( ) k = ±k F
24 (b),(c) (b)
25
26
27 TTF e e e e e e e e TF BEDT-TTF
28 (TMTF) + 2 X- H 3 C H 3 C e e e e TMTF CH 3 CH 3 X = ClO 4 T c = 1.4 K TMTF e (1980)
29 BEDT-TTF Cava (1978) BEDT-TTF (BEDT-TTF) 2 ClO 4 (TCE) 0.5 : 1.4 K (,1982)
30 BEDT-TTF T c 14.1 K BEDT-TTF 70%
31
32
33
34 a1 = ae1, a2 = ae2 e1, e2:, y b1 = (2 /a)e1, b2 = (2 /a)e2 a1 b1 = 2 a1 b2 = 0 a2 b1 = 0 a2 b2 = 2
35 TTF
36 Molecular orbital calculation for a single moleculel (Extended Hückel method) T. Mori et al., Bull. Chem. oc. Jpn., 57, 627 (1984) HOMO Donor LUMO Acceptor BEDT-TTF HOMO Intermolecular overlap integrals t = E Transfer integrals Tight-binding method Band structure and Fermi surface EDT-TTF
37 BEDT-TTF HOMO elative change of the overlap as a function of the intermolecular sulfur-sulfur distance, compared with the overlap 0 at 0 = 3.80 Å
38 -(BEDT-TTF) 2 I 3
39 -(BEDT-TTF) 2 I 3 (upper band)
40 BEDT-TTF "-type -, -type -type
41 M(dmit) 2, M = Ni, Pd DMET-TF,-DMBEDT-TTF BET BEDO-TTF DMET BEDT-TTF Acceptors Donors DTEDT e e e e Me Me Me Me Me Me Me Me M O O O O e e Me Me e e e e Me e e Me e e Me Me TMET-TF e e BEDe-TTF e e e e EET-TTF e e e e e e BDA-TTP MDT-TTF TMTF C 60 TMTTF MDT-TF meso-dmbedt-ttf Me Me O O DOHT
42
43
44 TTF ( ) BEDT-TTF
45 BEDT-TTF - perylene H H H H H H H H H H H H H H H H H H H H H H H
46 BEDT-TTF TTT
47 e NC e NC CN CN CPDT-TF TCNQ Overlap integrals of HOMO (x10-3 ) b1 = 17.6, b2 = 22.4, p = 17.9, q = 3.0, r = -4.7 Overlap integrals of LUMO (x10-3 ) c1 = 15.7, c2 = 12.9, p = -0.8, q = 0.12
48
49 BEDT-TTF -(BEDT-TTF) 2 X
50 Mott BEDT-TTF U/W 1 U: W:
51 TTF I II III IV
52 BEDT-TTF TTF 2,5-bis(1,3-dithiol-2-ylidene)- 1,3,4,6-tetrathiapentalene (BDT-TTP or simply TTP) TTP
53 O O + P(OEt) O O + O = CN, CF 3, CO 2 Me.. humaker, E. M. Engler et al., J. Chem. oc., Chem. Commun., 1979, 516 J. Am. Chem. oc., 1980, 102, TTF CV X CT
54 BDT-TTP Y. Misaki, et. al., Chem. Lett., (1992). Zn (Et 4 N) 2 p-acoc 6 H 4 CH 2 Cl acetone reflux p-acoc 6 H 4 CH 2 p-acoc 6 H 4 CH 2 95% Hg(OAc) 2 CHCl 3 -AcOH r.t. p-acoc 6 H 4 CH 2 p-acoc 6 H 4 CH 2 100% O / P(OEt) 3 CH 2 C 6 H 4 OAc-p 1) NaOMe/CH2 Cl 2 -MeOH, r.t. 110 C CH 2 C 6 H 4 OAc-p 2) ZnCl 2, Bu 4 NBr, r.t. 3) (Cl 47% 3 CO) 2 CO/THF, -78 C 50% O MeO 2 C MeO 2 C / P(OMe) 3 CO 2 Me LiBr H 2 O toluene CO HMPA 2 Me 110 C C 82% BDT-TTP 87% BDT-TTP TTF Kilburn et al. Tetrahedron. Lett., 33, 3923 (1992).
55 BDT-TTP Me = H, CO 2 Me, C n H 2n+1 (n = 2-6) - = -CH 2 -, -(CH 2 ) 2 -, -(CH 2 ) 3 - Me = H, CO 2 Me, Me - = -CH 2 -, -(CH 2 ) 2 -, -(CH 2 ) 3 -, -O(CH 2 ) 2 O- - = -(CH 2 ) 2 -, -(CH 2 ) 3 - O Me O = H, CO 2 Me, eme - = -CH 2 -, -(CH 2 ) 2 -, -O(CH 2 ) 2 O- Me = H, CO 2 Me, Me, eme - = -CH 2 -, -(CH 2 ) 2 -, -O(CH 2 ) 2 O- = H, CO 2 Me, Me, eme - = -CH 2 -, -(CH 2 ) 2 -, -O(CH 2 ) 2 O- = H, CO 2 Me, Me, eme - = -CH 2 -, -(CH 2 ) 2 -, -O(CH 2 ) 2 O- = H, CO 2 Me, Me - = -CH 2 -, -(CH 2 ) 2 -, -(CH 2 ) 3 -, ' e MeO 2 C e ' Me Me e e = Me, Me ' = Me, Et, Pr n = H, Me - = -(CH 2 ) 3 -, -(CH 2 ) 4 -, -O(CH 2 ) 2 O- e = H, Me - = -(CH 2 ) 3 -, -(CH 2 ) 4 -, -O(CH 2 ) 2 O- e e = Me - = -(CH 2 ) 3 -, -(CH 2 ) 4 -, -O(CH 2 ) 2 O- MeO 2 C Mee Mee e = H, Me - = -(CH 2 ) 3 -, -(CH 2 ) 4 -, -O(CH 2 ) 2 O- e e = Me - = -O(CH 2 ) 2 O- e e e EtO 2 C e = H, CO 2 Me e e = H, CO 2 Me EtO 2 C = Me, Et, C 6 H n 13
56 Table. edox Potentials of TTP and Its elated Compounds in PhCN (V v. CE, Pt electrode, 25 C) Compound E1 E2 E3 E4 E2-E1 TTP a) +1.13a) 0.18 TTF Me Me a) 0.31 MeDT-TTF Me Me a) Irreversible step. Anodic peak potentials.
57 Me Me Me Me I 3 TTM-TTP Mott D 0 D +2 D +1 + esistivity / cm (TTM-TTP)I 3 (TTM-TTP)(I 3 ) 5/3 Temperature / K rt = 700 cm K
58 BDT-TTP a1 = 25.1, a2 = 25.3, p1 = 7.9, p2 = 8.6, c = 0.8 a1 a2 a/p 3-4
59 X X Y Y X = Y =, BDT-TTP X =, Y = e, T-TTP X = Y = e, BD-TTP BDT-TTP (T-TTP, BD-TTP) (ClO 4, BF 4, eo 4 ) (PF 6, AsF 6, bf 6, TaF 6 ) (Au(CN) 2 ) (NO 3 ) (e 6 6 Cl 8, Mo 6 Cl 14 ) BEDT-TTF
60 PF 6 - Au(CN) 2 - e 6 6 Cl Å 6.2 Å 7.3 Å D : A = 2 : 1 D : A = 3 : 1 D : A = 6 : 1 (BDT-TTP) 1/2+ (BDT-TTP) 1/3+ (BDT-TTP) 1/3+
61 TTP side-byside
62 CH-T-TTP e e Au(CN) 2 2 -Type salts CH-TTP 2 X X = ClO 4, (I 3 ) 0.62 CH-T-TTP e e 2 X X = AsF 6, Au(CN) 2 elf-aggregation to adopt -type structure
63 Me Me e e TMET-T-TTP 2 TCNQ -Type salts Me Me TMET-TTP (X) m X = AuI 2, PF 6, eo 4, ClO 4 Me e Me TME-TTP e I 3 4 Me Me TMET-T-TTP e e TCNQ 2 elf-aggregation to adopt -type structure
64 O O EO-TTP 2 AsF 6 (bf 6 ) 0.4 CPEO-TTP O O a1 a2
65 Effect of methythio group teric hindrance CH 3 >> -(CH 2 ) 4 - Molecular packing trongly dimerized type Me Me e O e O TMEO-T-TTP AsF 6 2
66 BDT-TTP CH-TTP O O EO-TTP e e O O Me Me TMEO-T-TTP a1 a2
67 X X X X X X X = O,, e X = O, X =, e X X = O, CH CH CH CH CH X CH CH X CH X =, CH=CH TTP
68 DTEDT HOMO DTEDT DTEDT BDT-TTP BDT-TTP 0.08 Normalized esistivity eo 4 rt = cm -1 bf 6 I GaCl 4 T / K AsF esistivity / cm T / K DTEDT (DTEDT) 3 Au(CN) 2 (T c = 4 K)
69 DTEDT Au(CN) 2 3 DTEDT
70 Me e e Me Me e e Me (TMTF) 2 X T c ~ 1K ~ ~ (BEDT-TTF) 2 X T c ~ 10K M 3 C 60 T c > 30K T c TTP ide-by-side X X =, TPDT-TTP X = O, PDT-TTP
71 O PD-TTP e e 2 AsF 6 X e e CH 3 CH 3 A 2 X = O, TM-PD, A = bf 6, ClO 4, eo 4 X =, TM-TPD, A = AsF 6 O M-PDT eme eme (PF 6 )(PhCl) X
72 (PD-TTP) 2 AsF 6 O PD-TTP e e AsF A.... Crystal data: triclinic, space Group P 1 a = (7) Å b = (8) Å c = (2) Å = (6) = (8) = (3) V =787.6(1) Å 3 Z = 1 = Two-dimensional conducting sheet Head-to-tail overlap mode in the stack O-H hydrogen bond between conducting sheet H-F hydrogen bond between donor and anion
73 (PD-TTP) 2 AsF 6 O PD-TTP e e AsF 6 2 X X A m X =, e A: various anions X X X X 3 A X =, A = Au(CN) 2 X = e, A =TaF 6 O e e 2 AsF 6 e e TCNQ
74 (PD-TTP) 2 AsF 6 The intermoleculer overlap integral (x10-3) b1 = 10.0, b2 = 8.7, p1 = 3.1, p2 = 4.9, a = 1.2
75 (PD-TTP) 2 AsF 6
76 (TM-TPD) 2 AsF 6 e e TM-TPD CH 3 CH 3 AsF 6 2 "edge-to-side" " " O TM-PD e e CH 3 CH 3 2 X (X = ClO 4, eo 4, PF 6, bf 6 ) " "
77 (TM-TPD) 2 AsF 6
78 (TM-PD) 2 X (TM-PD) 2 AsF 6
79 (M-PDT) 2 AsF 6 (PhCl) side-by-side e---e : 3.694(2), 3.738(2) A ( ) cf. vdw radius; e : 1.90 A "edge-to-edge" (= bc ) rt = 4.8 cm -1, E a = ev 1:1
80 (M-PDT) 2 AsF 6 (PhCl) O M-PDT eme eme " "edge-to-edge" ( 30-40% ) The intermolecular overlap integrals c1 = 6.3, c2 = 8.1, p1 = -2.3, p2 = 0.00, b = -0.8 (x10-3).
81 O PD-TTP e e 2 AsF 6 O TM-PD e e Me Me 2 bf 6 O M-PDT eme eme PF 6 (PhCl) m side-by-side side-by-side side-by-side side-to-edge e-e edge-to-edge
82 Next Targets -Type structure with larger interlayer interaction O e e O O "Windmill" type structure with higher 3D character O e e Me Me e e e e Me Me Psedo "-type structure with higher 2D character O eme eme O TeMe TeMe
83 Yamada et al Angew. Chem. Int. Ed. Engl.,38, 810 (1999) BDA-TTP (BDA-TTP) 2 X (X = PF 6, AsF 6, bf 6 ) Yamada et al. J. Am. Chem. oc., 123, 4174 (2001). O ugawara et al. N N+ O_ Yamada et. al Chem. Coomun., 1996, 2517 BDT-TTP Kobayashi et al. ynth. Met., in press N N O Me e Takahashi et al. O Ni Tanaka et al., cience, 291, 285 (2001) Me e Yamada et al. J Org. Chem., 61, 3987 (1996)
84 ummary BDT-TTP BDT-TTP
85 TTF DTEDT O X X X =, PDT-TTP X = e, PD-TTP = H, Me, eme PDT-TTP, PD-TTP
86 TTP (
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