Synthesis of Aromatic Thiolate-Protected Gold Nanomolecules by Core Conversion: The Case of Au 36 (SPh- t Bu) 24

Ultrasmall nanomolecules (<2 nm) such as Au (SCH CH Ph) , Au (SCH CH Ph) , and Au (SCH CH Ph) are well studied and can be prepared using established synthetic procedures. No such synthetic protocols that result in high yield products from commercially available starting materials exist for Au (SP...

Full description

Saved in:
Bibliographic Details
Published inLangmuir Vol. 33; no. 30; pp. 7446 - 7451
Main Authors Theivendran, Shevanuja, Dass, Amala
Format Journal Article
LanguageEnglish
Published United States 01.08.2017
Online AccessGet full text

Cover

Abstract Ultrasmall nanomolecules (<2 nm) such as Au (SCH CH Ph) , Au (SCH CH Ph) , and Au (SCH CH Ph) are well studied and can be prepared using established synthetic procedures. No such synthetic protocols that result in high yield products from commercially available starting materials exist for Au (SPh-X) . Here, we report a synthetic procedure for the large-scale synthesis of highly stable Au (SPh-X) with a yield of ∼42%. Au (SPh-X) was conveniently synthesized by using tert-butylbenzenethiol (HSPh-tBu, TBBT) as the ligand, giving a more stable product with better shelf life and higher yield than previously reported for making Au (SPh) from thiophenol (PhSH). The choice of thiol, solvent, and reaction conditions were modified for the optimization of the synthetic procedure. The purposes of this work are to (1) optimize the existing procedure to obtain stable product with better yield, (2) develop a scalable synthetic procedure, (3) demonstrate the superior stability of Au (SPh-tBu) when compared to Au (SPh) , and (4) demonstrate the reproducibility and robustness of the optimized synthetic procedure.
AbstractList Ultrasmall nanomolecules (<2 nm) such as Au (SCH CH Ph) , Au (SCH CH Ph) , and Au (SCH CH Ph) are well studied and can be prepared using established synthetic procedures. No such synthetic protocols that result in high yield products from commercially available starting materials exist for Au (SPh-X) . Here, we report a synthetic procedure for the large-scale synthesis of highly stable Au (SPh-X) with a yield of ∼42%. Au (SPh-X) was conveniently synthesized by using tert-butylbenzenethiol (HSPh-tBu, TBBT) as the ligand, giving a more stable product with better shelf life and higher yield than previously reported for making Au (SPh) from thiophenol (PhSH). The choice of thiol, solvent, and reaction conditions were modified for the optimization of the synthetic procedure. The purposes of this work are to (1) optimize the existing procedure to obtain stable product with better yield, (2) develop a scalable synthetic procedure, (3) demonstrate the superior stability of Au (SPh-tBu) when compared to Au (SPh) , and (4) demonstrate the reproducibility and robustness of the optimized synthetic procedure.
Author Theivendran, Shevanuja
Dass, Amala
Author_xml – sequence: 1
  givenname: Shevanuja
  surname: Theivendran
  fullname: Theivendran, Shevanuja
  organization: Department of Chemistry and Biochemistry, University of Mississippi, Oxford, Mississippi 38677, United States
– sequence: 2
  givenname: Amala
  orcidid: 0000-0001-6942-5451
  surname: Dass
  fullname: Dass, Amala
  organization: Department of Chemistry and Biochemistry, University of Mississippi, Oxford, Mississippi 38677, United States
BackLink https://www.ncbi.nlm.nih.gov/pubmed/28715219$$D View this record in MEDLINE/PubMed
BookMark eNp9kM1OwzAQhC1URH_gDRDyEQ4pdpzEdW-lgoJUQaWWc2Q7GxqU2JWdIPXtMbS9cOCyq13NjDTfEPWMNYDQNSVjSmJ6L7Uf19J8NF3lxlwRSig_QwOaxiRKJzHvoQHhCYt4krE-Gnr_SQgRLBEXqB9PeNBRMUC79d60W_CVx7bEM2cb2VYab7aVrWUL0crZFnQLBV7YusCv0tjG1qC7GjxWezy3DsIwX-B8Zc00OMMtPfzGdZhl-Ha92ka4xQ_dHY6TS3ReytrD1XGP0PvT42b-HC3fFi_z2TLSlAoRxQCKgKZME-AFFzwTQFRRpqqkaUZYLFJN0yI8Ei4VVSrJJkIxUaqCs5RQNkI3h9xdpxoo8p2rGun2-al6EEwPAu2s9w7KXFdtKG9N62RV55TkP5zzwDk_cc6PnIM5-WM-5f9r-waNHITq
CitedBy_id crossref_primary_10_1021_acs_langmuir_7b03080
crossref_primary_10_1021_jacs_7b08516
crossref_primary_10_1039_C9NR10522K
crossref_primary_10_1007_s10876_018_1469_0
crossref_primary_10_1039_D3NR02617E
crossref_primary_10_1246_bcsj_20180357
crossref_primary_10_1021_acs_jpcc_1c10335
crossref_primary_10_1021_jacs_7b08651
crossref_primary_10_1021_acs_jpcc_9b09060
crossref_primary_10_1021_acs_jpclett_0c00199
crossref_primary_10_1016_j_jcis_2018_12_015
crossref_primary_10_3389_fchem_2018_00330
crossref_primary_10_1021_acs_accounts_8b00150
crossref_primary_10_1021_acs_jpcc_9b01953
crossref_primary_10_1021_acs_jpcc_4c04927
crossref_primary_10_1039_C8CP01564C
Cites_doi 10.1021/ja8005379
10.1021/cm200143s
10.1021/ja201685f
10.1016/j.addr.2008.03.016
10.1021/la9019475
10.1021/nn401971g
10.1021/acs.jpclett.7b00442
10.1021/nn800632j
10.1021/jp501073a
10.1126/sciadv.1500425
10.1021/jz301191t
10.1021/ar7002804
10.1002/anie.201202369
10.1021/la404618r
10.1021/jacs.5b12747
10.1021/ar200331z
10.1021/jacs.6b04835
10.1021/nn901137h
10.1021/jp506508x
10.1002/adma.19960080513
10.1021/ja800561b
10.1002/anie.201207098
10.1021/acs.jpclett.5b00780
10.1021/ja5103025
10.1021/ja710323t
10.2147/NSA.S3788
10.1021/acs.analchem.6b03428
10.1021/ja711298b
10.1002/anie.200901185
10.1021/jz501941p
10.1021/acs.jpcc.5b08193
10.1021/ja053915s
10.1039/c3cp52837e
10.1039/c2nr30900a
10.1021/ja103592z
10.1021/ja0782448
10.1021/la700753u
10.1021/jp993229d
10.1517/17425241003777010
10.1021/ja513152h
10.1021/ja1099006
10.1021/ar100048c
ContentType Journal Article
DBID AAYXX
CITATION
NPM
DOI 10.1021/acs.langmuir.7b01017
DatabaseName CrossRef
PubMed
DatabaseTitle CrossRef
PubMed
DatabaseTitleList PubMed
Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1520-5827
EndPage 7451
ExternalDocumentID 28715219
10_1021_acs_langmuir_7b01017
Genre Research Support, U.S. Gov't, Non-P.H.S
Journal Article
GroupedDBID ---
-~X
.K2
4.4
53G
55A
5GY
5VS
7~N
AABXI
AAHBH
AAYXX
ABBLG
ABJNI
ABLBI
ABMVS
ABQRX
ABUCX
ACGFS
ACJ
ACNCT
ACS
ADHLV
AEESW
AENEX
AFEFF
AGXLV
AHGAQ
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
BAANH
CITATION
CS3
CUPRZ
DU5
EBS
ED~
EJD
F5P
GGK
GNL
IH9
IHE
JG~
RNS
ROL
TN5
UI2
UPT
VF5
VG9
W1F
YQT
~02
NPM
ID FETCH-LOGICAL-c1199-2eeb0ec13c0e7d79769e0bdf5bf15603295c15ddf547ab1bb4689b39fbd735013
IEDL.DBID ACS
ISSN 0743-7463
IngestDate Thu Jan 02 23:10:19 EST 2025
Thu Apr 24 22:59:19 EDT 2025
Tue Jul 01 02:31:00 EDT 2025
IsPeerReviewed true
IsScholarly true
Issue 30
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c1199-2eeb0ec13c0e7d79769e0bdf5bf15603295c15ddf547ab1bb4689b39fbd735013
ORCID 0000-0001-6942-5451
PMID 28715219
PageCount 6
ParticipantIDs pubmed_primary_28715219
crossref_citationtrail_10_1021_acs_langmuir_7b01017
crossref_primary_10_1021_acs_langmuir_7b01017
ProviderPackageCode CITATION
AAYXX
PublicationCentury 2000
PublicationDate 2017-08-01
PublicationDateYYYYMMDD 2017-08-01
PublicationDate_xml – month: 08
  year: 2017
  text: 2017-08-01
  day: 01
PublicationDecade 2010
PublicationPlace United States
PublicationPlace_xml – name: United States
PublicationTitle Langmuir
PublicationTitleAlternate Langmuir
PublicationYear 2017
References ref9/cit9
ref6/cit6
ref36/cit36
ref3/cit3
ref27/cit27
ref18/cit18
ref11/cit11
ref25/cit25
ref16/cit16
ref29/cit29
ref32/cit32
ref23/cit23
ref39/cit39
ref14/cit14
ref8/cit8
ref5/cit5
ref31/cit31
ref2/cit2
ref43/cit43
ref37/cit37
ref28/cit28
ref40/cit40
ref20/cit20
ref17/cit17
ref10/cit10
ref26/cit26
ref35/cit35
ref19/cit19
ref21/cit21
ref12/cit12
ref15/cit15
ref42/cit42
ref41/cit41
ref22/cit22
ref13/cit13
ref33/cit33
ref4/cit4
ref30/cit30
ref1/cit1
ref24/cit24
ref38/cit38
ref44/cit44
ref7/cit7
References_xml – ident: ref12/cit12
  doi: 10.1021/ja8005379
– ident: ref21/cit21
  doi: 10.1021/cm200143s
– ident: ref27/cit27
  doi: 10.1021/ja201685f
– ident: ref1/cit1
  doi: 10.1016/j.addr.2008.03.016
– ident: ref8/cit8
  doi: 10.1021/la9019475
– ident: ref30/cit30
  doi: 10.1021/nn401971g
– ident: ref44/cit44
  doi: 10.1021/acs.jpclett.7b00442
– ident: ref3/cit3
  doi: 10.1021/nn800632j
– ident: ref33/cit33
  doi: 10.1021/jp501073a
– ident: ref23/cit23
  doi: 10.1126/sciadv.1500425
– ident: ref37/cit37
  doi: 10.1021/jz301191t
– ident: ref6/cit6
  doi: 10.1021/ar7002804
– ident: ref42/cit42
  doi: 10.1002/anie.201202369
– ident: ref41/cit41
  doi: 10.1021/la404618r
– ident: ref24/cit24
  doi: 10.1021/jacs.5b12747
– ident: ref15/cit15
  doi: 10.1021/ar200331z
– ident: ref25/cit25
  doi: 10.1021/jacs.6b04835
– ident: ref20/cit20
  doi: 10.1021/nn901137h
– ident: ref28/cit28
  doi: 10.1021/jp506508x
– ident: ref10/cit10
  doi: 10.1002/adma.19960080513
– ident: ref31/cit31
  doi: 10.1021/ja800561b
– ident: ref29/cit29
  doi: 10.1002/anie.201207098
– ident: ref40/cit40
  doi: 10.1021/acs.jpclett.5b00780
– ident: ref39/cit39
  doi: 10.1021/ja5103025
– ident: ref43/cit43
  doi: 10.1021/ja710323t
– ident: ref19/cit19
  doi: 10.1021/ja8005379
– ident: ref2/cit2
  doi: 10.2147/NSA.S3788
– ident: ref35/cit35
  doi: 10.1021/acs.analchem.6b03428
– ident: ref9/cit9
  doi: 10.1021/ja711298b
– ident: ref4/cit4
  doi: 10.1002/anie.200901185
– ident: ref11/cit11
  doi: 10.1021/jz501941p
– ident: ref16/cit16
  doi: 10.1021/acs.jpcc.5b08193
– ident: ref38/cit38
  doi: 10.1021/ja053915s
– ident: ref13/cit13
  doi: 10.1039/c3cp52837e
– ident: ref14/cit14
  doi: 10.1039/c2nr30900a
– ident: ref32/cit32
  doi: 10.1021/ja103592z
– ident: ref22/cit22
  doi: 10.1021/ja0782448
– ident: ref17/cit17
  doi: 10.1021/la700753u
– ident: ref36/cit36
  doi: 10.1021/jp993229d
– ident: ref7/cit7
  doi: 10.1517/17425241003777010
– ident: ref26/cit26
  doi: 10.1021/ja513152h
– ident: ref5/cit5
  doi: 10.1021/ja1099006
– ident: ref18/cit18
  doi: 10.1021/ar100048c
SSID ssj0009349
Score 2.22754
Snippet Ultrasmall nanomolecules (<2 nm) such as Au (SCH CH Ph) , Au (SCH CH Ph) , and Au (SCH CH Ph) are well studied and can be prepared using established synthetic...
SourceID pubmed
crossref
SourceType Index Database
Enrichment Source
StartPage 7446
Title Synthesis of Aromatic Thiolate-Protected Gold Nanomolecules by Core Conversion: The Case of Au 36 (SPh- t Bu) 24
URI https://www.ncbi.nlm.nih.gov/pubmed/28715219
Volume 33
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3NS8MwFA-yi178_phf5OBBD5lNkzaLNx3qENTBJngrzRcbajvWVph_vUm7KlNEvRRaXh7lJeT9Xl7e7wFwZKxXVLFqIyo5Q5Qqg7hUDDkmPB7EWAvmaodv78LuA715DB4_A8WvGXwfn8Yya7mzu5diNGkx4TjRyuJxRh1V_nmn_8mxSyq061g3GQ1JXSn3g5I5TzSHKUvfcrUC7usKnepKyVOryEVLvn0nbPzjb6-C5RnMhOfVulgDCzpZB4udurvbBhj3p4nFftkog6mxcmlJ3QoHw5GNdXONehV_g1bwOn1W0G7C6UvVSVdnUExhJ51o-0heq_O2MzvSvluXWKorIAnhcb83RDCHF8UJ9OkmeLi6HHS6aNZ9AUmMOUe-1sLTEhPpaaaYhS1ce0KZQBhXfU18HkgcKPuBslhgIWjY5oJwIxRz2UqyBRpJmugdADENJFNGyTYj1LRZHHhUeVgGNKSYG9wEpJ6JSM6oyV2HjOeoTJH7OLLWjGprRjNrNgH6GDWuqDl-kd-uJvlD2kWLFr7w3X9q2gNLvvPu5T3AfdDIJ4U-sNgkF4flinwH2NTgeg
linkProvider American Chemical Society
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Synthesis+of+Aromatic+Thiolate-Protected+Gold+Nanomolecules+by+Core+Conversion%3A+The+Case+of+Au+36+%28SPh-+t+Bu%29+24&rft.jtitle=Langmuir&rft.au=Theivendran%2C+Shevanuja&rft.au=Dass%2C+Amala&rft.date=2017-08-01&rft.issn=0743-7463&rft.eissn=1520-5827&rft.volume=33&rft.issue=30&rft.spage=7446&rft.epage=7451&rft_id=info:doi/10.1021%2Facs.langmuir.7b01017&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_acs_langmuir_7b01017
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0743-7463&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0743-7463&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0743-7463&client=summon