Mesogenic BODIPYs: an investigation of the correlation between liquid crystalline behaviour and fluorescence intensity View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2011-03-07

AUTHORS

Michael Benstead, Geraldine A. Rosser, Andrew Beeby, Georg H. Mehl, Ross W. Boyle

ABSTRACT

A series of mesogenic molecules based on the 4,4′-difluoro-3a,4a-diaza-s-indacene (BODIPY) fluorophore have been synthesised and characterised. Each compound consists of one mesogenic unit, based on a cyanobiphenyl core, and one fluorophore, of varying alkyl substitution. The compounds were prepared by microwave-assisted palladium-catalyzed couplings (Suzuki and Sonogashira) due to slow reaction rates under conventional heating conditions. The effect of increasing the molecular length was also investigated by incorporating an ethynyl unit between the mesogen and the fluorophore. The molecules self-assemble into monotropic nematic phases which were identified by optical polarising microscopy (OPM) and differential scanning calorimetry (DSC). The compounds were found to display varying degrees of fluorescence quantum yield dependant on the number of alkyl substituents attached to the fluorophore. A relationship was observed between the nematic phase stability and fluorescence intensity of the compounds with increasing alkyl substitution causing an increase in fluorescence intensity due to restriction of the 8-phenyl ring rotation while simultaneously disrupting nematic phase formation, causing a reduction in nematic range. Temperature-dependant fluorescence measurements were also acquired along with fluorescence measurements of four of the synthesised BODIPYs dissolved in a commercial nematic liquid crystal (BL024) and incorporated into a twisted nematic cell. More... »

PAGES

992-999

Identifiers

URI

http://scigraph.springernature.com/pub.10.1039/c0pp00388c

DOI

http://dx.doi.org/10.1039/c0pp00388c

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1002629344

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/21380443


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/02", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Physical Sciences", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0299", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Other Physical Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Department of Chemistry, University of Hull, Kingston-Upon-Hull, HU6 7RX, East Yorkshire, UK", 
          "id": "http://www.grid.ac/institutes/grid.9481.4", 
          "name": [
            "Department of Chemistry, University of Hull, Kingston-Upon-Hull, HU6 7RX, East Yorkshire, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Benstead", 
        "givenName": "Michael", 
        "id": "sg:person.014060026213.77", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014060026213.77"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Chemistry, Durham University, DH1 3LE, Durham, UK", 
          "id": "http://www.grid.ac/institutes/grid.8250.f", 
          "name": [
            "Department of Chemistry, Durham University, DH1 3LE, Durham, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Rosser", 
        "givenName": "Geraldine A.", 
        "id": "sg:person.01130276003.16", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01130276003.16"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Chemistry, Durham University, DH1 3LE, Durham, UK", 
          "id": "http://www.grid.ac/institutes/grid.8250.f", 
          "name": [
            "Department of Chemistry, Durham University, DH1 3LE, Durham, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Beeby", 
        "givenName": "Andrew", 
        "id": "sg:person.01041405257.29", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01041405257.29"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Chemistry, University of Hull, Kingston-Upon-Hull, HU6 7RX, East Yorkshire, UK", 
          "id": "http://www.grid.ac/institutes/grid.9481.4", 
          "name": [
            "Department of Chemistry, University of Hull, Kingston-Upon-Hull, HU6 7RX, East Yorkshire, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Mehl", 
        "givenName": "Georg H.", 
        "id": "sg:person.01102572504.24", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01102572504.24"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Chemistry, University of Hull, Kingston-Upon-Hull, HU6 7RX, East Yorkshire, UK", 
          "id": "http://www.grid.ac/institutes/grid.9481.4", 
          "name": [
            "Department of Chemistry, University of Hull, Kingston-Upon-Hull, HU6 7RX, East Yorkshire, UK"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Boyle", 
        "givenName": "Ross W.", 
        "id": "sg:person.01270352613.45", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01270352613.45"
        ], 
        "type": "Person"
      }
    ], 
    "datePublished": "2011-03-07", 
    "datePublishedReg": "2011-03-07", 
    "description": "A series of mesogenic molecules based on the 4,4\u2032-difluoro-3a,4a-diaza-s-indacene (BODIPY) fluorophore have been synthesised and characterised. Each compound consists of one mesogenic unit, based on a cyanobiphenyl core, and one fluorophore, of varying alkyl substitution. The compounds were prepared by microwave-assisted palladium-catalyzed couplings (Suzuki and Sonogashira) due to slow reaction rates under conventional heating conditions. The effect of increasing the molecular length was also investigated by incorporating an ethynyl unit between the mesogen and the fluorophore. The molecules self-assemble into monotropic nematic phases which were identified by optical polarising microscopy (OPM) and differential scanning calorimetry (DSC). The compounds were found to display varying degrees of fluorescence quantum yield dependant on the number of alkyl substituents attached to the fluorophore. A relationship was observed between the nematic phase stability and fluorescence intensity of the compounds with increasing alkyl substitution causing an increase in fluorescence intensity due to restriction of the 8-phenyl ring rotation while simultaneously disrupting nematic phase formation, causing a reduction in nematic range. Temperature-dependant fluorescence measurements were also acquired along with fluorescence measurements of four of the synthesised BODIPYs dissolved in a commercial nematic liquid crystal (BL024) and incorporated into a twisted nematic cell.", 
    "genre": "article", 
    "id": "sg:pub.10.1039/c0pp00388c", 
    "inLanguage": "en", 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1029729", 
        "issn": [
          "1474-905X", 
          "1474-9092"
        ], 
        "name": "Photochemical & Photobiological Sciences", 
        "publisher": "Springer Nature", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "6", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "10"
      }
    ], 
    "keywords": [
      "optical polarising microscopy", 
      "differential scanning calorimetry", 
      "alkyl substitution", 
      "commercial nematic liquid crystal", 
      "liquid crystalline behavior", 
      "monotropic nematic phase", 
      "fluorescence intensity", 
      "nematic phase formation", 
      "nematic phase stability", 
      "palladium-catalyzed coupling", 
      "conventional heating conditions", 
      "fluorescence quantum yield", 
      "slow reaction rate", 
      "fluorescence measurements", 
      "mesogenic units", 
      "cyanobiphenyl core", 
      "crystalline behavior", 
      "indacene (BODIPY) fluorophore", 
      "mesogenic molecules", 
      "ethynyl units", 
      "polarising microscopy", 
      "molecular length", 
      "alkyl substituents", 
      "scanning calorimetry", 
      "nematic liquid crystals", 
      "nematic phase", 
      "liquid crystals", 
      "reaction rate", 
      "quantum yield", 
      "nematic range", 
      "ring rotation", 
      "fluorophores", 
      "compounds", 
      "phase formation", 
      "phase stability", 
      "twisted nematic cell", 
      "molecules", 
      "heating conditions", 
      "mesogens", 
      "diaza", 
      "BODIPY", 
      "substituents", 
      "calorimetry", 
      "substitution", 
      "nematic cell", 
      "crystals", 
      "microscopy", 
      "stability", 
      "yield", 
      "measurements", 
      "formation", 
      "intensity", 
      "phase", 
      "units", 
      "coupling", 
      "core", 
      "range", 
      "series", 
      "behavior", 
      "investigation", 
      "conditions", 
      "reduction", 
      "length", 
      "effect", 
      "degree", 
      "increase", 
      "rate", 
      "rotation", 
      "cells", 
      "correlation", 
      "number", 
      "relationship", 
      "restriction", 
      "microwave-assisted palladium-catalyzed couplings", 
      "Temperature-dependant fluorescence measurements", 
      "synthesised BODIPYs"
    ], 
    "name": "Mesogenic BODIPYs: an investigation of the correlation between liquid crystalline behaviour and fluorescence intensity", 
    "pagination": "992-999", 
    "productId": [
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1002629344"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1039/c0pp00388c"
        ]
      }, 
      {
        "name": "pubmed_id", 
        "type": "PropertyValue", 
        "value": [
          "21380443"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1039/c0pp00388c", 
      "https://app.dimensions.ai/details/publication/pub.1002629344"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2022-01-01T18:24", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-springernature-scigraph/baseset/20220101/entities/gbq_results/article/article_529.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://doi.org/10.1039/c0pp00388c"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1039/c0pp00388c'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1039/c0pp00388c'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1039/c0pp00388c'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1039/c0pp00388c'


 

This table displays all metadata directly associated to this object as RDF triples.

169 TRIPLES      21 PREDICATES      102 URIs      94 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1039/c0pp00388c schema:about anzsrc-for:02
2 anzsrc-for:0299
3 schema:author N57984a9b123149259c372e522482a1c6
4 schema:datePublished 2011-03-07
5 schema:datePublishedReg 2011-03-07
6 schema:description A series of mesogenic molecules based on the 4,4′-difluoro-3a,4a-diaza-s-indacene (BODIPY) fluorophore have been synthesised and characterised. Each compound consists of one mesogenic unit, based on a cyanobiphenyl core, and one fluorophore, of varying alkyl substitution. The compounds were prepared by microwave-assisted palladium-catalyzed couplings (Suzuki and Sonogashira) due to slow reaction rates under conventional heating conditions. The effect of increasing the molecular length was also investigated by incorporating an ethynyl unit between the mesogen and the fluorophore. The molecules self-assemble into monotropic nematic phases which were identified by optical polarising microscopy (OPM) and differential scanning calorimetry (DSC). The compounds were found to display varying degrees of fluorescence quantum yield dependant on the number of alkyl substituents attached to the fluorophore. A relationship was observed between the nematic phase stability and fluorescence intensity of the compounds with increasing alkyl substitution causing an increase in fluorescence intensity due to restriction of the 8-phenyl ring rotation while simultaneously disrupting nematic phase formation, causing a reduction in nematic range. Temperature-dependant fluorescence measurements were also acquired along with fluorescence measurements of four of the synthesised BODIPYs dissolved in a commercial nematic liquid crystal (BL024) and incorporated into a twisted nematic cell.
7 schema:genre article
8 schema:inLanguage en
9 schema:isAccessibleForFree false
10 schema:isPartOf N6b492db3747f4c259f3d94cea14ea01d
11 Nfcc80e517ea84455a6f7189faf218d24
12 sg:journal.1029729
13 schema:keywords BODIPY
14 Temperature-dependant fluorescence measurements
15 alkyl substituents
16 alkyl substitution
17 behavior
18 calorimetry
19 cells
20 commercial nematic liquid crystal
21 compounds
22 conditions
23 conventional heating conditions
24 core
25 correlation
26 coupling
27 crystalline behavior
28 crystals
29 cyanobiphenyl core
30 degree
31 diaza
32 differential scanning calorimetry
33 effect
34 ethynyl units
35 fluorescence intensity
36 fluorescence measurements
37 fluorescence quantum yield
38 fluorophores
39 formation
40 heating conditions
41 increase
42 indacene (BODIPY) fluorophore
43 intensity
44 investigation
45 length
46 liquid crystalline behavior
47 liquid crystals
48 measurements
49 mesogenic molecules
50 mesogenic units
51 mesogens
52 microscopy
53 microwave-assisted palladium-catalyzed couplings
54 molecular length
55 molecules
56 monotropic nematic phase
57 nematic cell
58 nematic liquid crystals
59 nematic phase
60 nematic phase formation
61 nematic phase stability
62 nematic range
63 number
64 optical polarising microscopy
65 palladium-catalyzed coupling
66 phase
67 phase formation
68 phase stability
69 polarising microscopy
70 quantum yield
71 range
72 rate
73 reaction rate
74 reduction
75 relationship
76 restriction
77 ring rotation
78 rotation
79 scanning calorimetry
80 series
81 slow reaction rate
82 stability
83 substituents
84 substitution
85 synthesised BODIPYs
86 twisted nematic cell
87 units
88 yield
89 schema:name Mesogenic BODIPYs: an investigation of the correlation between liquid crystalline behaviour and fluorescence intensity
90 schema:pagination 992-999
91 schema:productId N16878d7729cb45a3a16964c7d4d3ced8
92 N3b8adc58bf564efe924434d5bc1cbdc8
93 Nd89a03291de649ffac61c2dd193ec836
94 schema:sameAs https://app.dimensions.ai/details/publication/pub.1002629344
95 https://doi.org/10.1039/c0pp00388c
96 schema:sdDatePublished 2022-01-01T18:24
97 schema:sdLicense https://scigraph.springernature.com/explorer/license/
98 schema:sdPublisher Nfd916ed9e6ed42618989a38500042073
99 schema:url https://doi.org/10.1039/c0pp00388c
100 sgo:license sg:explorer/license/
101 sgo:sdDataset articles
102 rdf:type schema:ScholarlyArticle
103 N0c742b2d3d87456e97e1c647caa68371 rdf:first sg:person.01270352613.45
104 rdf:rest rdf:nil
105 N16878d7729cb45a3a16964c7d4d3ced8 schema:name doi
106 schema:value 10.1039/c0pp00388c
107 rdf:type schema:PropertyValue
108 N3b8adc58bf564efe924434d5bc1cbdc8 schema:name dimensions_id
109 schema:value pub.1002629344
110 rdf:type schema:PropertyValue
111 N57984a9b123149259c372e522482a1c6 rdf:first sg:person.014060026213.77
112 rdf:rest N762f215235f24d31a4595804fdf142aa
113 N5fc4facd819f48dfb92263c307c333d8 rdf:first sg:person.01102572504.24
114 rdf:rest N0c742b2d3d87456e97e1c647caa68371
115 N6b492db3747f4c259f3d94cea14ea01d schema:volumeNumber 10
116 rdf:type schema:PublicationVolume
117 N762f215235f24d31a4595804fdf142aa rdf:first sg:person.01130276003.16
118 rdf:rest N9159f36b18cf4c30aa1afa2c5e344a70
119 N9159f36b18cf4c30aa1afa2c5e344a70 rdf:first sg:person.01041405257.29
120 rdf:rest N5fc4facd819f48dfb92263c307c333d8
121 Nd89a03291de649ffac61c2dd193ec836 schema:name pubmed_id
122 schema:value 21380443
123 rdf:type schema:PropertyValue
124 Nfcc80e517ea84455a6f7189faf218d24 schema:issueNumber 6
125 rdf:type schema:PublicationIssue
126 Nfd916ed9e6ed42618989a38500042073 schema:name Springer Nature - SN SciGraph project
127 rdf:type schema:Organization
128 anzsrc-for:02 schema:inDefinedTermSet anzsrc-for:
129 schema:name Physical Sciences
130 rdf:type schema:DefinedTerm
131 anzsrc-for:0299 schema:inDefinedTermSet anzsrc-for:
132 schema:name Other Physical Sciences
133 rdf:type schema:DefinedTerm
134 sg:journal.1029729 schema:issn 1474-905X
135 1474-9092
136 schema:name Photochemical & Photobiological Sciences
137 schema:publisher Springer Nature
138 rdf:type schema:Periodical
139 sg:person.01041405257.29 schema:affiliation grid-institutes:grid.8250.f
140 schema:familyName Beeby
141 schema:givenName Andrew
142 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01041405257.29
143 rdf:type schema:Person
144 sg:person.01102572504.24 schema:affiliation grid-institutes:grid.9481.4
145 schema:familyName Mehl
146 schema:givenName Georg H.
147 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01102572504.24
148 rdf:type schema:Person
149 sg:person.01130276003.16 schema:affiliation grid-institutes:grid.8250.f
150 schema:familyName Rosser
151 schema:givenName Geraldine A.
152 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01130276003.16
153 rdf:type schema:Person
154 sg:person.01270352613.45 schema:affiliation grid-institutes:grid.9481.4
155 schema:familyName Boyle
156 schema:givenName Ross W.
157 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01270352613.45
158 rdf:type schema:Person
159 sg:person.014060026213.77 schema:affiliation grid-institutes:grid.9481.4
160 schema:familyName Benstead
161 schema:givenName Michael
162 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014060026213.77
163 rdf:type schema:Person
164 grid-institutes:grid.8250.f schema:alternateName Department of Chemistry, Durham University, DH1 3LE, Durham, UK
165 schema:name Department of Chemistry, Durham University, DH1 3LE, Durham, UK
166 rdf:type schema:Organization
167 grid-institutes:grid.9481.4 schema:alternateName Department of Chemistry, University of Hull, Kingston-Upon-Hull, HU6 7RX, East Yorkshire, UK
168 schema:name Department of Chemistry, University of Hull, Kingston-Upon-Hull, HU6 7RX, East Yorkshire, UK
169 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...