Synthesis and structures of thieno[2,3-b]thiophene incorporated [3.3]dithiacyclophanes. Enhanced first hyperpolarizability in an unsymmetrically polarized cyclophane

Sabir H. Mashraqui; Yogesh S. Sangvikar; Auke Meetsma

doi:10.1016/j.tetlet.2006.05.098

Synthesis and structures of thieno[2,3-b]thiophene incorporated [3.3]dithiacyclophanes. Enhanced first hyperpolarizability in an unsymmetrically polarized cyclophane

Sabir H. Mashraqui^*, Yogesh S. Sangvikar, Auke Meetsma

^*Corresponding author for this work

Stratingh Institute for Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

37 Citations (Scopus)

Abstract

Dithiacyclophanes incorporating thieno[2,3-b]thiophene have been synthesized. in order to investigate the nonlinear optical properties of donor-acceptor cyclophane 7. Cyclophane 7 displayed significantly higher first hyperpolarizability beta (21.6 x 10(-30) esu) compared to model 10 (9.58 x 10(-30) esu). Relatively higher in 7 presumably arises from an extra electron redistribution arising from through-space charge transfer, a feature lacking in 10. Moreover. the thermal decomposition temperature of 7 (300 degrees C) is higher than that reported for the NLO prototype DAN (295 degrees C). (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5599-5602
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	31
DOIs	https://doi.org/10.1016/j.tetlet.2006.05.098
Publication status	Published - 31-Jul-2006

Keywords

cyclophanes
thieno[2.3-b]thiophene
X-ray structures
UV-vis
first hyperpolarizability
through-space charge redistribution
NONLINEAR-OPTICAL CHROMOPHORES
PARACYCLOPHANE
DELOCALIZATION

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Synthesis and structures of thieno[2,3-b]thiophene incorporated [3.3]dithiacyclophanes
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CCDC 297140: Experimental Crystal Structure Determination
Mashraqui, S. H. (Contributor), Sangvikar, Y. S. (Contributor) & Meetsma, A. (Contributor), University of Groningen, 1-Feb-2006
DOI: 10.5517/cc9z65m
Dataset
CCDC 297142: Experimental Crystal Structure Determination
Mashraqui, S. H. (Contributor), Sangvikar, Y. S. (Contributor) & Meetsma, A. (Contributor), University of Groningen, 1-Feb-2006
DOI: 10.5517/cc9z67p
Dataset
CCDC 297141: Experimental Crystal Structure Determination
Mashraqui, S. H. (Contributor), Sangvikar, Y. S. (Contributor) & Meetsma, A. (Contributor), University of Groningen, 1-Feb-2006
DOI: 10.5517/cc9z66n
Dataset

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@article{8c84560e1860430baa507b3ae51b1175,

title = "Synthesis and structures of thieno[2,3-b]thiophene incorporated [3.3]dithiacyclophanes. Enhanced first hyperpolarizability in an unsymmetrically polarized cyclophane",

abstract = "Dithiacyclophanes incorporating thieno[2,3-b]thiophene have been synthesized. in order to investigate the nonlinear optical properties of donor-acceptor cyclophane 7. Cyclophane 7 displayed significantly higher first hyperpolarizability beta (21.6 x 10(-30) esu) compared to model 10 (9.58 x 10(-30) esu). Relatively higher in 7 presumably arises from an extra electron redistribution arising from through-space charge transfer, a feature lacking in 10. Moreover. the thermal decomposition temperature of 7 (300 degrees C) is higher than that reported for the NLO prototype DAN (295 degrees C). (c) 2006 Elsevier Ltd. All rights reserved.",

keywords = "cyclophanes, thieno[2.3-b]thiophene, X-ray structures, UV-vis, first hyperpolarizability, through-space charge redistribution, NONLINEAR-OPTICAL CHROMOPHORES, PARACYCLOPHANE, DELOCALIZATION",

author = "Mashraqui, {Sabir H.} and Sangvikar, {Yogesh S.} and Auke Meetsma",

year = "2006",

month = jul,

day = "31",

doi = "10.1016/j.tetlet.2006.05.098",

language = "English",

volume = "47",

pages = "5599--5602",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "31",

}

Synthesis and structures of thieno[2,3-b]thiophene incorporated [3.3]dithiacyclophanes. Enhanced first hyperpolarizability in an unsymmetrically polarized cyclophane. / Mashraqui, Sabir H.; Sangvikar, Yogesh S.; Meetsma, Auke.
In: Tetrahedron Letters, Vol. 47, No. 31, 31.07.2006, p. 5599-5602.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Synthesis and structures of thieno[2,3-b]thiophene incorporated [3.3]dithiacyclophanes. Enhanced first hyperpolarizability in an unsymmetrically polarized cyclophane

AU - Mashraqui, Sabir H.

AU - Sangvikar, Yogesh S.

AU - Meetsma, Auke

PY - 2006/7/31

Y1 - 2006/7/31

N2 - Dithiacyclophanes incorporating thieno[2,3-b]thiophene have been synthesized. in order to investigate the nonlinear optical properties of donor-acceptor cyclophane 7. Cyclophane 7 displayed significantly higher first hyperpolarizability beta (21.6 x 10(-30) esu) compared to model 10 (9.58 x 10(-30) esu). Relatively higher in 7 presumably arises from an extra electron redistribution arising from through-space charge transfer, a feature lacking in 10. Moreover. the thermal decomposition temperature of 7 (300 degrees C) is higher than that reported for the NLO prototype DAN (295 degrees C). (c) 2006 Elsevier Ltd. All rights reserved.

AB - Dithiacyclophanes incorporating thieno[2,3-b]thiophene have been synthesized. in order to investigate the nonlinear optical properties of donor-acceptor cyclophane 7. Cyclophane 7 displayed significantly higher first hyperpolarizability beta (21.6 x 10(-30) esu) compared to model 10 (9.58 x 10(-30) esu). Relatively higher in 7 presumably arises from an extra electron redistribution arising from through-space charge transfer, a feature lacking in 10. Moreover. the thermal decomposition temperature of 7 (300 degrees C) is higher than that reported for the NLO prototype DAN (295 degrees C). (c) 2006 Elsevier Ltd. All rights reserved.

KW - cyclophanes

KW - thieno[2.3-b]thiophene

KW - X-ray structures

KW - UV-vis

KW - first hyperpolarizability

KW - through-space charge redistribution

KW - NONLINEAR-OPTICAL CHROMOPHORES

KW - PARACYCLOPHANE

KW - DELOCALIZATION

U2 - 10.1016/j.tetlet.2006.05.098

DO - 10.1016/j.tetlet.2006.05.098

M3 - Article

SN - 0040-4039

VL - 47

SP - 5599

EP - 5602

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Synthesis and structures of thieno[2,3-b]thiophene incorporated [3.3]dithiacyclophanes. Enhanced first hyperpolarizability in an unsymmetrically polarized cyclophane

Abstract

Keywords

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Datasets

CCDC 297140: Experimental Crystal Structure Determination

CCDC 297142: Experimental Crystal Structure Determination

CCDC 297141: Experimental Crystal Structure Determination

Cite this