2003
DOI: 10.1039/b307901p
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The first liquid-crystalline, expanded porphyrinsElectronic supplementary information (ESI) available: synthetic procedures, hydrazinophyrin characterisation, and crystal structure data. See http://www.rsc.org/suppdata/cc/b3/b307901p/

Abstract: Aliphatic derivatives of hydrazinophyrin, a new type of tetrapyrrolic macrocycle prepared by the condensation of 2,5-diformylpyrroles with hydrazine, exhibit liquid crystalline properties as judged from polarising optical microscopy; these hydrazinophyrins appear to be the first mesogens derived from an expanded porphyrin core.

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Cited by 36 publications
(17 citation statements)
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“…); IR; n(Kbr)/cm -1 3743, 3673,2921,2886,1732,1622,1575,1456,1393,1266,1213,1057,1003,875,773,646 and 478; (992.62) C 79.80,H 8.12,N 5.64;found: C 79.72,H 8.10,: To a solution of 4-tert-butyl-2-methylphenol 5 (2.19 g, 13.3 mmol) in CF 3 COOH (22 cm 3 ) was added a hexamethylenetetramine (9.35 g, 66.7 mmol) and stirred for 24 h at 90°C. Then a reaction mixture was cooled and poured into 10% HCl aqueous solution (150 cm 3 Preparation of 7: To a solution of 6 (330 mg, 1.73 mmol) in CH 2 Cl 2 (5 cm 3 ) was added o-phenylenediamine (140 mg, 1.29 mmol) and stirred for 24 h at room temperature. The reaction mixture was condensed in vacuum to afford a residue.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…); IR; n(Kbr)/cm -1 3743, 3673,2921,2886,1732,1622,1575,1456,1393,1266,1213,1057,1003,875,773,646 and 478; (992.62) C 79.80,H 8.12,N 5.64;found: C 79.72,H 8.10,: To a solution of 4-tert-butyl-2-methylphenol 5 (2.19 g, 13.3 mmol) in CF 3 COOH (22 cm 3 ) was added a hexamethylenetetramine (9.35 g, 66.7 mmol) and stirred for 24 h at 90°C. Then a reaction mixture was cooled and poured into 10% HCl aqueous solution (150 cm 3 Preparation of 7: To a solution of 6 (330 mg, 1.73 mmol) in CH 2 Cl 2 (5 cm 3 ) was added o-phenylenediamine (140 mg, 1.29 mmol) and stirred for 24 h at room temperature. The reaction mixture was condensed in vacuum to afford a residue.…”
Section: Methodsmentioning
confidence: 99%
“…Development of conjugated macrocycles is a rapidly growing area of interest because they may form the basis of catalytic, 1 magnetic, 2 liquid crystalline, 3 pharmaceutical, 4 and supramolecular materials. 5 Aldehyde and amine repeat formation and cleavage of Schiff base combination (imino group) reversibly under suitable reaction conditions, finally, reach the thermodynamic most stable state.…”
mentioning
confidence: 99%
“…Am oderate yield for 6 may be attributed to the longerr eactiont ime. Furthermore, the direct reductiveM cMurry coupling of 3,4-dimethoxypyrrole-2,5-dialdehyde [9] led to 6 in 1.4 %y ield as the only non-polymer product. [4]…”
Section: Synthesis Of Expanded Porphycenesmentioning
confidence: 99%
“…[20,21] The most significant LC behaviour was found by peripheral modification of octa-substituted and meso-tetraphenylporphyrinic derivatives. [2,[20][21][22][23][24][25][26][27][28] Additionally,s ome tetrapyrrolic macrocyclesp eripherally substituted have LCs properties and exhibit columnar mesophases. [29,30] Following our research interests in discotic LC and luminescent materials, [31][32][33] and considering the potential of functionalised meso-tetraarylporphyrins in this field, [34] we decided to prepareaseries of easily accessible porphyrins containing four (3a,b)o re ight (3c,d)a liphatic amide chains with different lengths.…”
Section: Introductionmentioning
confidence: 99%