Star-Shaped Conjugated Systems
Abstract
:- Table of Content
- 1. Introduction
- 2. Molecular Architecture and Conjugation
- 3. Three-arm Systems with one Central Atom
- 3.1. [3]Star Systems with Methylium Core
- 3.2. [3]Star Systems with Boron Core
- 3.3. [3]Star Compounds with Nitrogen Core
- 4. Star Compounds with a Benzene Core
- 4.1. Three-armed Stars (C-4)
- 4.1.1. Structure and Conjugation
- 4.1.2. Synthesis
- 4.1.3. Three-arm Stars with Benzene Centers and Materials Science
- 4.2. Four-arm Systems-Tetrasubstituted Benzene (C-5)
- 4.2.1. Structure and Conjugation
- 4.2.2. Synthesis
- 4.2.3. Four-arm Stars with Benzene Centers and Materials Science
- 4.3. Six-arm Systems-Hexasubstituted Benzenes (C-6)
- 4.3.1. Structure and Conjugation of Parent Systems
- 4.3.2. Synthesis of the Parent Systems
- 4.3.3. Hexaarm Stars with Benzene Centers and Materials Science
- 5. Compounds with Heterocyclic Cores
- 5.1. Pyridine-based Stars (C-7-A-6, C-7-A-7)
- 5.2. Stars with a Pyrimidine Core
- 5.3. Pyrazine as Core (C-10-A-6)
- 5.4. 1,3,5-Triazine as Core
- 5.5. Borazine as a Core
- 6. Condensed Ring Systems as Cores
- 6.1. Triphenylene Star Compounds (C-12)
- 6.1.1. Structures and Synthesis
- 6.1.2. Triphenylene Derivatives and Materials Science
- 6.2. Hexaazatriphenylene (C-13-A-3 and C-13-A-6)
- 6.3. Triazatruxenes (C-14-A-3 and C-14-A-8)
- 6.4. Tristriazolotriazines (C-15-A-3 and C-15-A-9)
- 7. Summary and Conclusion
1. Introduction
2. Molecular Architecture and Conjugation
Generation n | Core Symmetry D3h C2v Cs |
1 2 3 4 | 2 4 8 12 32 64 88 256 512 696 512 1024 |
3. Three-Arm Systems with One Central Atom
3.1. [3]Star Systems with Methylium Core
3.2. [3]Star Systems with Boron Core
3.3. [3]Star Compounds with Nitrogen Core
4. Star Compounds with a Benzene Core
4.1. Three-armed Stars (C-4)
4.1.1. Structure and Conjugation
Compounda | Substituents E, R Solvent, T (K) | Absorption λmax [nm] (ε [Lcm-1mol-1]) | Emission λmax [nm] (Quantum yield Ф) | Reference | |
24a | star | H (dioxane) | 250 (59,600) | 354 (0.10) | [62] |
linear | H (dioxane) | 246 (18,600) | 316 (0.18) | [62] | |
25a | star | tristyryl (hexane, 293 K) | 317 (47,863) | 410 | [63] [64] |
linear | H (methylpentanes, 295 K) EPA,c 77 K | 294 (26,000) 303 (51,500) | 347 343 | [65] [66] | |
26a | star | H CHCl3, 295 K | 305 (85,100) | 353 (0.15) | [67] |
linear | H CHCl3 EPA,c 77 K | 300 (24,000) 284 (42,900) 302 (44,500) | — 326 | [66] | |
27a | star | H DMF | 337 (142,000) | — | [70] |
linear | H DMF | 328 (45,200) | — | [70] | |
28a | star | H acetonitril | 308 (158,000) | 365 (0.92) | [68] |
linear | H EPA,c 77 K | 307 (55,000) 325 (51,400) | 352 | [66] | |
24b n = 2 | star | H dioxane | 288 (103,000) | 364 (0.27) | [62] |
linear | H dioxane | 276 (30,200) | 342 (0.55) | [62] | |
24c n = 3 | star | H dioxane | 307 (136,000) | 375 (0.71) | [62] |
linear | H dioxane | 294 (48,600) | 369 (0.71) | [62] | |
25c n = 0 | star | Trisdodecyloxy-phenylethenyl CHCl3, rt | 331 (81,000) | 426b | [69] |
25d n = 1 | star | Trisdodecyloxy-phenylethenyl CHCl3, rt | 376 (170,000) | 447b | [69] |
linear | Trisdodecyloxy-phenylethenyl,R = Methyl | 366 (64,000) | [70] | ||
25e n = 2 | star | Trisdodecyloxy-phenylethenyl CHCl3, rt | 397 (313,000) | - | [69] |
linear | Trisdodecyloxy-phenylethenyl, R = CH2OH CH2Cl2, 298 K | 390 (67,000) | 468 nm | [71] | |
26b n = 1 | star | H, OCH3 CHCl3, 295 K | 334 (64,600) | 384 (0.46) | [67] |
26c n = 2 | star | H, OCH3 CHCl3, 295 K | 380 (128,800) | 409 (0.85) | [67] |
26d n = 3 | star | H, OCH3 CHCl3, 295 K | 426 (195,000) | 464 (0.98) | [67] |
linear | H, OCH3 CHCl3, 295 K | 390 (56,200) | 430 (0.81) | [67] | |
26e n = 0 | star | 2-methoxyphenylethynyl, OCH3 CHCl3, 295 K | 314 (58,900) | 359 (0.24) | [67] |
26f n = 1 | star | 2-methoxyphenylethynyl, OCH3 CHCl3, 295 K | 377 (104,700) | 406 (0.83) | [67] |
26g n = 2 | star | 2-methoxyphenylethynyl, OCH3 CHCl3, 295 K | 405 (128,800) | 433 (0.97) | [67] |
29a n = 1 | star | 3,4-dibutoxy-phenyl | 340 | [72] | |
linear | 3,4-dibutoxy-phenyl | 325 | [72] | ||
29b n = 2 | star | 3,4-dibutoxy-phenyl | 360 | [72] | |
linear | 3,4-dibutoxy-phenyl | 350 | [72] | ||
29c n = 3 | star | 3,4-dibutoxy-phenyl | 380 | [72] | |
linear | 3,4-dibutoxy-phenyl | 375 | [72] |
4.1.2. Synthesis
4.1.3. Three-arm Stars with Benzene Centers and Materials Science
Compound | Thermotropic behavior (T [°C] / ΔH [kJ/mol]a | Ref. |
25b (n = 1) | Cr 38/39 Colhd 75/10 I | [88,111] |
25c (n = 2) | g 21 (Tg) Colhd 108/4 I | [89] |
25d (n = 3) | g 55 (Tg) Colhd 199/3 I | [69] |
25e (n = 1) | g -15 (Tg) Colhd 74/4 I | [111] |
25f (n = 2) | g 21 (Tg) LD 129/3 I | [89] |
25g (n = 1) | Cr 189/45 I | [111] |
25h (n = 2) | Cr 216/40 I | [89] |
25i (n = 1) | g 140 (Tg) ND 260 Ib | [113] |
25j (n = 2) | g 246 (Tg) ND 296 Ib | [113] |
25k (n = 1) | Cr 209/40 ND 232/1 I | [112] |
25l (n = 1) | g 2 (Tg) ND 114/0.2 ND’ 126/0.4 I | [112] |
25m | g 140 (Tg) N 226 Ib | [113] |
4.2. Four-arm Systems-Tetrasubstituted Benzene (C-5)
4.2.1. Structure and Conjugation
Compounda | Substituents E, R Solvent, T (K) | Absorption λmax [nm] (ε [Lcm-1mol-1]) | Emission λmax [nm] (Quantum yield Ф) | Ref. | |
55b (n = 2) | star | H (CHCl3) | 276 (-) | 410 | [158] |
linear | H (CHCl3) | 309 (log4,8) | 386 (0.90) | [159] | |
56a (n = 1) | star | H (Toluene, 293 K) (Toluene 77K) | 337/370 (S) 350/365(S)/375(S) | 450/472 442/463 | [64] |
linear | H (Hexane, rt) | 350 | 417 | [160] | |
57a | star | H CHCl3 | 315(134,900)/350 | 391 (0.57) | [143] [159] |
linear | H CHCl3 | 328 (38,900) | 348 (0.83) | [159] |
4.2.2. Synthesis
4.2.3. Four-arm Stars with Benzene Centers and Materials Science
4.3. Six-arm Systems-Hexasubstituted Benzenes (C-6)
4.3.1. Structure and Conjugation of Parent Systems
Compounda | Substituents E | Absorption λmax [nm] | Emission λmax [nm] | References | |
66a | star | H | 249 | 337 | [197] |
linear | H | 280 | 342 | [159] | |
67b | star | 4-dodecyloxy | 342 | - | [198] |
linear | 369 | - | |||
68a | star | H | 349 | 449 | [143,159] |
linear | H | 328 | 348 | [159] | |
69c | star | 4-tert-butylphenyl | 385/415 | - | [199] |
linear | phenyl | 335/360 | - | [200] |
4.3.2. Synthesis of the Parent Systems
4.3.3. Hexaarm Stars with Benzene Centers and Materials Science
Ea | X | Transition Temperatures /°Cb | Ea | X | Transition Temperatures /°Cb |
n-pentyl | H | Cr 170 ND 185 I | hexyloxy | H | Cr 144 ND 216 I |
n-hexyl | H | Cr 124 ND 142 I | heptyloxy | H | Cr 109 ND 193 I |
n-heptyl | H | Cr 98 ND 131 I | meta hexyloxy | H | Cr 87 I |
n-octyl | H | Cr 80 ND 96 I | ortho hexyloxy | H | Cr 63 I |
n-nonyl | H | Cr 67 ND 83 I | octyloxy | CH3 | Cr 95 ND 176 I |
n-decyl | H | Cr 71 (ND 54) I | 3,7-dimethyl-octyloxy | H | Cr 80 ND 124 I |
n-dodecyl | H | no LC | 3,7-dimethyl-octyloxy | CH3 | Cr 71 ND 147-160 I |
5. Compounds with Heterocyclic Cores
5.1. Pyridine-based Stars (C-7-A-6, C-7-A-7):
5.2. Stars with a Pyrimidine Core
5.3. Pyrazine as Core (C-10-A-6)
Compound | Transition T ΔH (cal/g) | Transition T ΔH (cal/g) |
92d: 3,4-dihexyloxy | Cryst → Col 102 °C (14.0) | Col → i 210 °C (0.4) |
92e: 3,4-didecyloxy | Cryst → Col 101 °C (19.3) | Col → i 173 °C (1.5) |
92f: 3,4-didodecyloxy | Cryst → Col 95 °C (18.8) | Col → i 172 °C (0.7) |
5.4. 1,3,5-Triazine as Core
- a)
- ΔE (n+1) < ΔE (n) monotonous bathochromic shift
- b)
- ΔE (n+1) > ΔE (n) monotonous hypsochromic shift
- c)
- ΔE (n+1) ≈ ΔE (n) borderline case between a) and b)
- a)
- ΔE goes through a minimum for a certain n
Star | 2. compound | Tm /°C | Tc /°C | Structure |
121a | 70.4 | 154.6 | Colhd | |
121b | 54.4 | 90.8 | Dhd | |
121c | 68.4 | 76.9 | Dro | |
121a | 123a | 32.4 | 64.8 | Colhd |
121a | 123b | 34.5 | 75.1 | Colhd |
121a | 123c | 18.7 | 73.6 | Colhd |
121a | 123d | 62.2 | 88.7 | Colrd |
121a | 124 | 68.1 | 110.4 | SmA |
121b | 124 | 68.6 | 115.9 | SmA |
121b | 125 | 93.7 | 147.2 | Colr |
5.5. Borazine as a Core
6. Condensed Ring Systems as Cores
6.1. Triphenylene Star Compounds (C-12)
6.1.1. Structures and Synthesis
6.1.2. Triphenylene Derivatives and Materials Science
Compound | E | X | Y | phase transitions [°C] | reference |
129e | OC6H13 | OC6H13 | H | Cr 111 Col 126 I Cr 65 Colh 135 I | [335,336] |
129f | OC8H17 | OC8H17 | H | Cr 85 Col 104 I | [335] |
129g | OC10H21 | OC10H21 | H | Cr 74 Col 103 I | [335] |
129h | OC12H25 | OC12H25 | H | Cr 47 Col 101 I | [335] |
129i | OC6H13 | H | H | Cr 153 I | [332] |
129j | OC11H23 | H | H | Cr 66 I | [332] |
129k | H | OC6H13 | H | Cr 11 I | [337] |
129l | H | H | OC6H13 | Cr 81 I | [337] |
129m | C9H19 | H | H | Cr 59 I | [332] |
129n | C12H25 | H | H | Cr 37 I | [332] |
129m + 133a 1 :1 | Cr 66 Colh 155 I | [336] | |||
132a | C9H19 | Cr 81 I | [336,338] | ||
132a + 133a 1:1 | Colh 240 I | [336,338] |
6.2. Hexaazatriphenylenec (C-13-A-3 and C-13-A-6)
R = | λmax /nm (toluene) | ε / l/mol°cm | λFmax / nm(toluene) | Φ | λFmax / nm (CH2Cl2) | Φ | |
132e | H | 366 | 21.000 | 419 | 0.01 | 424 | 0.03 |
132k | -N(C6H5)2 | 453 | 98.000 | 502 | 0.95 | 563 | 0.75 |
132d | -C6H5 | 392 | 68.000 | 438 | 0.43 | 449 | 0.50 |
132b | -C6H4- N(C6H5)2 | 417 | 129.000 | 501 | 0.96 | 624 | 0.27 |
6.3. Triazatruxenes (C-14-A-3 and C-14-A-8)
6.4. Tristriazolotriazines (C-15-A-3 and C-15-A-9)
7. Summary and Conclusion
References and Notes
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Detert, H.; Lehmann, M.; Meier, H. Star-Shaped Conjugated Systems. Materials 2010, 3, 3218-3330. https://doi.org/10.3390/ma3053218
Detert H, Lehmann M, Meier H. Star-Shaped Conjugated Systems. Materials. 2010; 3(5):3218-3330. https://doi.org/10.3390/ma3053218
Chicago/Turabian StyleDetert, Heiner, Matthias Lehmann, and Herbert Meier. 2010. "Star-Shaped Conjugated Systems" Materials 3, no. 5: 3218-3330. https://doi.org/10.3390/ma3053218