Bent and Twisted: Synthesis of an Alkoxy-Substituted (1,5)Naphthalene-paracyclophanediene.

Arielle Mann, Matthew D Hannigan, Bianca L Dumlao, Chunhua T Hu, Marcus Weck

Abstract read

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Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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0cells of the map it votes in

1citing papers in PubMed

–field-weighted citation impact

1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

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3 · Its place in the literature

Who cites it

1 citing paper in PubMed.

Strain, Chain, Repeat: Synthesis and Optoelectronic Properties of Poly(Naphthalene Benzene Vinylene)s.ACS macro letters · 2026
Article

4 · The record

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5 · Who and what money

Authors and funding

5 authors.

Arielle MannDepartment of Chemistry and Molecular Design Institute, New York University, New York, New York 10003, United States.ORCID 0000-0001-9832-6436

Matthew D HanniganDepartment of Chemistry and Molecular Design Institute, New York University, New York, New York 10003, United States.ORCID 0000-0002-2267-1388

Bianca L DumlaoDepartment of Chemistry and Molecular Design Institute, New York University, New York, New York 10003, United States.

Chunhua T HuDepartment of Chemistry and Molecular Design Institute, New York University, New York, New York 10003, United States.ORCID 0000-0002-8172-2202

Marcus WeckDepartment of Chemistry and Molecular Design Institute, New York University, New York, New York 10003, United States.ORCID 0000-0002-6486-4268

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

This contribution describes the synthesis of [2.2](1,5)naphthalenoparacyclophane-1,13-diene in four steps from 1,5-bis(bromomethyl)naphthalene and 1,4-benzenedimethanethiol. Consisting of 2,6-dioctyloxynaphthalene and benzene moieties, the effects of differing arene size on the structure, strain energy, and chemical reactivity of the cyclophanediene are examined. Despite a strain energy of 24.3 kcal/mol, the naphthalenoparacyclophanediene was unreactive toward a library of olefin metathesis catalysts. This diminished reactivity can be explained by the steric hindrance of the twisted olefin. Incorporation of an electron donor (naphthalene) into the rigid paracyclophanediene structure can allow for applications in optoelectronics, chiral ligands, and planar chiral materials.

Identifiers

PMID37647456

DOI10.1021/acs.joc.3c00880

PMCPMC10507662

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.