1994
DOI: 10.1007/bf02275501
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Molecular structures and packing arrangements of five 2,5-bis(aryl-2-vinyl)-1,4-dimethoxybenzene derivatives

Abstract: The crystal and molecular structures of five 2,5-bis(aryl-2-vinyl)-l,4-dimethoxybenzene derivatives la-le were determined by X-ray diffraction with respect to topochemical aspects. We found three types of packing arrangements: (1) a-type packing with 7 A. stacking axes, (2) /3-type packing with 4 A, stacking axes and (3) a third intermediate packing type. The intermolecular distances between the vinylic double bonds of all derivatives exceed the limits of 4 A. in the crystals. Therefore photochemical [2 +2]cyc… Show more

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Cited by 11 publications
(11 citation statements)
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References 13 publications
(5 reference statements)
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“…A, 1.414(2) A) and single (1.386 A) C-C bonds in the thiophene ring are very similar in length, in contrast to the strongly alternating pattern found in the absence of strong donor and acceptor substitution. [50][51][52] The patterns of bond lengths in 1 are similar to those seen in the structure of other related donor-acceptor chromophores with strong p-acceptors, such as IV (Fig. 4c).…”
Section: Crystal Structuresupporting
confidence: 73%
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“…A, 1.414(2) A) and single (1.386 A) C-C bonds in the thiophene ring are very similar in length, in contrast to the strongly alternating pattern found in the absence of strong donor and acceptor substitution. [50][51][52] The patterns of bond lengths in 1 are similar to those seen in the structure of other related donor-acceptor chromophores with strong p-acceptors, such as IV (Fig. 4c).…”
Section: Crystal Structuresupporting
confidence: 73%
“…0.1 A are found in fully quinoidal structures 49 ); the vinylene portion of the bridge shows a bond-length alternation (BLA) between formally double and single bonds of ca. 0.079 (6) A, a little lower than the >0.1 A found for -CH]CH-groups (including those linking aryl and thienyl groups) in the absence of significant zwitterionic contributions; [50][51][52] and the formally double (1.384(2)…”
Section: Crystal Structurementioning
confidence: 74%
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“…The “ortho” methoxy (O(1)) does not interact strongly with neighboring molecules but points the lone pairs on O toward the olefin on the same molecule (O(1)···H(9)C, 2.46 Å). The intermolecular O···H interaction in 4 is not present in the lattice of 1,4-distyryl 2,5-dimethoxybenzene ( HESMUN ) or any of the chlorinated derivatives of 1,4-distryl-2,5-dimethoxybenzene. ,
6 A layer of the structure of 1,4-bis(2,5-dimethoxystyryl)benzene ( 4 ) roughly in the bc plane. Annotated close contacts are of a distance of 2.56(4) Å.
…”
Section: Resultsmentioning
confidence: 99%
“…The solid-state structures and electronic properties of one particular class of these oligomeric organic semiconductors, viz. distyrylbenzenes, oligomeric derivatives of PPV [poly(pphenylene vinylene)], have already been extensively studied and the influence of substituents on the properties of the carbon backbone have been investigated (Baeke et al, 2007;Vande Velde et al, 2004;Vande Velde, Baeke et al 2005;Vande Velde, De Borger et al, 2005;Vande Velde et al, 2006;Irngartinger et al, 1994;Hakansson et al, 1992;Bartholomew et al, 2000a,b;Coates et al, 1998;Nohra et al, 2006;Renak et al, 1999;Sancho-Garcia et al, 2005;Zeller et al, 2005). However, keeping in mind the tunability of these materials, it is equally interesting to determine the effects of the replacement of the ethenylic -CH CH-link by other spacers such as -CH N-…”
Section: Commentmentioning
confidence: 99%