What have We Learned about Topochemical Diacetylene Polymerizations?

Curtis, Sean M.; Le, Nam Cao Hoai; Nguyen, Tam Luong; Ouyang, Xi; Tran, Tritan; Fowler, Frank W.; Lauher, Joseph W.

doi:10.1080/10610270412331328916

Cited by 38 publications

(35 citation statements)

References 10 publications

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“…(1); Y=O (2); Y=S (12) N2-C7-C7 i 113.12 (16) 113.41 (14) O2-C15-O3 123.95 (13) 124.20 (12) O2-C15-C14 124.46 (13) 124.16 (12) O3-C15-C14 111.57 (12) 111.58 (11) Symmetry operation i for (1) 2 -x, 2 -y, -z, for (2): 1 -x, 1 -y, -z formed between translationally related 4-nitrophenylacetic acid molecules, C-HÁÁÁp, between phenyl-H and the pyridyl ring, and pÁÁÁp interactions, between pyridyl residues and between phenyl rings, as shown in Fig. 8.…”

Section: Supramolecular Aggregationmentioning

confidence: 98%

“…Thus, oligomeric metal complexes [1][2][3] and coordination polymers [4][5][6] have been generated utilizing these molecules with a variety of metal centers. Cocrystals have also been prepared for the purpose evaluating concepts in halogen bonding [7,8], for example, but also with other species including carboxylic acids [9][10][11][12], the latter studies being directly relevant to the present study.…”

Section: Introductionmentioning

confidence: 99%

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Crystal and Molecular Structures of the 2:1 Cocrystal of 4-Nitrophenylacetic acid and N,N′-bis(pyridin-3-ylmethyl)oxalamide, and with the Thioxalamide Analogue

et al. 2012

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The common feature of each of the title 2:1 cocrystals is the formation of the O-HÁÁÁN(pyridyl) hydrogen bonds leading to three-molecule aggregates. The persistent formation of the O-HÁÁÁN(pyridyl) hydrogen bonds where other functionalities are present, e.g. amide, indicates the robustness of this supramolecular synthon. In the structure of the 2:1 4-nitrophenylacetic acid N,N 0 -bis (pyridin-3-ylmethyl)oxalamide cocrystal, (1), the amide-H forms a hydrogen bond with the hydroxyl group so that rows of N,N 0 -bis(pyridin-3-ylmethyl)oxalamide molecules are linked into a supramolecular tape via 4-nitrophenylacetic acid molecules. In the N,N 0 -bis(pyridin-3-ylmethyl)thioxalamide derivative, (2), the thioamide-H atom only forms an intramolecular N-HÁÁÁS contact. Nevertheless, a supramolecular tape is formed but mediated by C-HÁÁÁO(nitro) interactions. Compound (1) crystallizes in the triclinic space group P¯1 with a = 8.195(2) Å , b = 9.502(3) Å , c = 9.999(3) Å , a = 90.631(3)8, b = 102.796(5)8, c = 108.075(5)8, and Z = 1 (three molecule aggregate). Compound (2) also crystallizes in the triclinic space group P¯1 with a = 8.0772(12) Å , b = 10.2111(12) Å , c = 10.2563(17) Å , a = 71.319(10)8, b = 77.777(11)8, c = 67.660(9)8, and Z = 1 (three molecule aggregate).

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Section: Supramolecular Aggregationmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Crystal and Molecular Structures of the 2:1 Cocrystal of 4-Nitrophenylacetic acid and N,N′-bis(pyridin-3-ylmethyl)oxalamide, and with the Thioxalamide Analogue

et al. 2012

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“…The diyne systems are parallel as requested; nevertheless, the angle of the reactive carbons and mostly their distance separations are not favorable, being distorted and much too long, respectively (Figure 4). Topochemical polymerization of diacetylene is also prevented because there is no long range parallel stacking of diynes [58][59][60][61][62][63][64][65][66][67]. …”

Section: Crystallographic Studiesmentioning

confidence: 99%

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

et al. 2016

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Isomorphous crystals of two diacetylene derivatives with carbamate functionality (BocNH-CH 2 -diyne-X, where X = H or Br) have been obtained. The main feature of these structures is the original 2D arrangement (as supramolecular sheets or walls) in which the H bond and halogen bond have a prominent effect on the whole architecture. The two diacetylene compounds harbor neighboring carbamate (Boc protected amine) and conjugated alkyne functionalities. They differ only by the nature of the atom located at the penultimate position of the diyne moiety, either a hydrogen atom or a bromine atom. Both of them adopt very similar 2D wall organizations with antiparallel carbamates (as in antiparallel beta pleated sheets). Additional weak interactions inside the same walls between molecular bricks are H bond interactions (diyne-H¨¨¨O=C) or halogen bond interactions (diyne-Br¨¨¨O=C), respectively. Based on crystallographic atom coordinates, DFT (B3LYP/6-31++G(d,p)) and DFT (M06-2X/6-31++G(d,p)) calculations were performed on these isostructural crystals to gain insight into the intermolecular interactions.

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“…There are five co-crystals in the literature involving 4 LH2 and carboxylic acids, one of which is a monofunctional carboxylic acid [14] with the other four being bifunctional, having two carboxylic acid residues [24,35,36]. In the former, 4 LH2 is located about a centre of inversion and so in this 1:2 co-crystal, there is one independent molecule of (4-nitrophenyl)acetic acid [14].…”

Section: Co-crystalsmentioning

confidence: 99%

“…19b, and N,N'-bis(2-hydroxyethyl)oxalamide [35], the links between each of these co-formers are also of the type amide-N-H…O(amide). In an interesting variation, a polymer, namely poly(1,2-bis(2-carboxyethyl)tetra-1-en-3-yn-1,4-diyl, provides the bridges between amide tapes [36], Fig. 19c.…”

Section: Co-crystalsmentioning

confidence: 99%

13. Crystal chemistry of the isomeric N,N'-bis(pyridin-n-ylmethyl)-ethanediamides, n = 2, 3 or 4

Tiekink¹

2017

Multi-Component Crystals

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What have We Learned about Topochemical Diacetylene Polymerizations?

Cited by 38 publications

References 10 publications

Crystal and Molecular Structures of the 2:1 Cocrystal of 4-Nitrophenylacetic acid and N,N′-bis(pyridin-3-ylmethyl)oxalamide, and with the Thioxalamide Analogue

Crystal and Molecular Structures of the 2:1 Cocrystal of 4-Nitrophenylacetic acid and N,N′-bis(pyridin-3-ylmethyl)oxalamide, and with the Thioxalamide Analogue

Isomorphous Crystals from Diynes and Bromodiynes Involved in Hydrogen and Halogen Bonds

13. Crystal chemistry of the isomeric N,N'-bis(pyridin-n-ylmethyl)-ethanediamides, n = 2, 3 or 4

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