Synthesis of Solution-Processable Donor-Acceptor Pyranone Dyads for White Organic Light-Emitting Devices

Article abstract of DOI:10.1021/acs.joc.9b00293

A series of donor-acceptor pyranones (3a-m, 4a-h) were synthesized using α-oxo-ketene-S,S-acetal as the synthon for their application as emissive materials for energy-saving organic light-emitting devices (OLEDs). Among them, five pyranones 3f, 3g, 3h, 3m

Full text of DOI:10.1021/acs.joc.9b00293

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Article
Synthesis of Solution-Processable Donor-Acceptor
Pyranone dyads for White Organic Light Emitting Devices
CHANDRA PRAKASH SHARMA, Neeraj M. Gupta, Jagriti Singh, Rohit Ashok Kumar Yadav,
Deepak Kumar Dubey, Kundan Singh Rawat, Ajay Kumar Jha, Jwo-Huei Jou, and Atul Goel
J. Org. Chem., Just Accepted Manuscript • Publication Date (Web): 22 May 2019
Downloaded from http://pubs.acs.org on May 29, 2019
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&<&/1')<7=(,&%/&,1 0')0&'1(&% )* 15& *.E'(/.1&+ ?@AB% /),1.(,(,8 15& ,&4<2 %2,15&%(6&+ &=(11&'%$ M)
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3,&.1 *(<=C +&>(/&% )* .,.<)8)7% +2&%D Z1 =(851 E& +7& 1) 15& &**&/1(>& /.017'(,8 )* &:/(1),% *)'=&+
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.,15'./&,2<-02'.,),& .1 R 41MC &:5(E(1&+ 07'& 45(1& <(851 &=(%%(), 4(15 8))+ &:1&',.<
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[7.,17= &**(/(&,/2 .,+ E'(851,&%%D G5&%& 0'(=.'2 '&%7<1% (,+(/.1&+ 15.1 15& *<7)'&%/&,1 +),)'-
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<%"%-4+M H .,+ RTW dNX %0&/1'. 4&'& '&/)'+&+ .1 TKK .,+ UKK NH6 (, _'7;&' %0&/1')=&1&'D
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02'.,-Q-),&% M0,: .,+ N0,$ 4&'& %2,15&%(6&+ .//)'+(,8 1) 15& 0')/&+7'& +&%/'(E&+ &.'<(&'DUR G5&
+.1. )* .<< 15& %2,15&%(6&+ /)=0)7,+% .'& 8(>&, 5&'&D
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3RDUQ 8$ UPM 2(&<+Cf XE k KDTP 3/5<)')*)'=J=&15.,)<$ LLhR$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C
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QUU-QUY Wf N] 3A]ZC =J6 QSL aN n Hbnf ZX 3u_'C x k QQRU 3WdC$ RVRY 3W?C /=-Rf H
dNX 3UKK NH6$ BN]?-4@Ch R k QDSV 3%$ THC$ VDUR 3%$ RHC$ SDQL 3+$ Q k LDKY H6$ QHC$ SDTL
3+$ Q k LDKY H6$ QHC 00=f WyRHz dNX 3RKK NH6$ BN]?-4@Ch
/ k RUDL$ LRDT$ RKQDU$
RT
RRUDU$ RQUDY$ RQSDS$ RTYDK$ RULDS$ RPVDQ$ RPSDV$ RVRDL 00=f HXN] 3A]ZC /.</7<.1&+ *)'
WRTHSdQ?U]h QSLDKQST aN n HbnD I)7,+ QSLDKQSUD
^,UN,)*+(.(3$%"!*O,N,U:%#$!*#$'(O,T,(W(,T@,3!.0",M,/0.1("'#.'*% UM1O= m'&&,(%5 2&<<)4
3Q 8$ VKM 2(&<+Cf XE k KDUT 3/5<)')*)'=J=&15.,)<$ LLhR$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C
)
R
RSY-RSS Wf N] 3A]ZC =J6 QYQ aN n Hbnf ZX 3u_'C x k QQRY 3WdC$ RVRT 3W?C /=-Rf H
dNX 3UKK NH6$ BN]?-4@Ch R k QDST 3%$ THC$ VDQQ 3%$ RHC$ VDUU 31$ Q k SDS H6$ QHC$ SDRK-
SDRU 3=$ QHC 00=f RTWyRHz dNX 3RKK NH6$ BN]?-4@Ch
/ k RUDS$ SLDU$ LLDL$ RRUDP$ RRUDP$
RRYDS$ RRVDK$ RQYDS$ RTKDQ$ RTKDT$ RPVDP$ RYKDP$ RYTDS$ RYYDT$ RVQDK 00=f HXN] 3A]ZC
/.</7<.1&+ *)' WRTHSId?Q]h QYQDKTTS aN n HbnD I)7,+ QYQDKTTTD
^,UN,/$*(.(3$%"!*O,N,U:%#$!*#$'(O,T,(W(,T@,3!.0",M,/0.1("'#.'*% UM/O=NS0 g&<<)4 %)<(+
3RDS 8$ YKM 2(&<+Cf XE k KDPU 3/5<)')*)'=J=&15.,)<$ LLhR$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C
)
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QUK-QUQ Wf N] 3A]ZC =J6 QVS aN n Hbnf ZX 3u_'C x k QQRV 3WdC$ RVQU 3W?C /=-Rf H
dNX 3UKK NH6$ BN]?-4@Ch R k QDST 3%$ THC$ VDQP 3%$ RHC$ VDYY 3+$ Q k SDS H6$ QHC$ SDKY
3+$ Q k SDS H6 QHC 00=f HXN] 3A]ZC /.</7<.1&+ *)' WRTHSW<d?Q]h QVSDKKUT aN n HbnD
I)7,+ QVSDKKTLD
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3RDSQ 8$ PQM 2(&<+Cf XE k KDTS 3/5<)')*)'=J=&15.,)<$ LLhR$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C
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QTK-QTQ Wf N] 3A]ZC =J6 TQQ aN n Hbnf ZX 3u_'C x k QQRT 3WdC$ RYLV 3W?C /=-Rf H
dNX 3UKK NH6$ BN]?-4@Ch R k QDST 3%$ THC$ VDQY 3%$ RHC$ VDVL 3+$ Q k SDS H6$ QHC$ VDLS
3+$ Q k SDS H6 QHC 00=f HXN] 3A]ZC /.</7<.1&+ *)' WRTHS_'d?Q]h TQRDLPTV aN n HbnD
I)7,+ TQRDLPTLD
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N,U:%#$!*#$'(O,T,(W(,^,U3,#(*!*O,T@,3!.0",M,/0.1("'#.'*% UM%O= m'&&,(%5 2&<<)4 %)<(+
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QQK-QQQ Wf N] 3A]ZC =J6 QPS aN n Hbnf ZX 3u_'C x k QQRQ 3WdC$ RYLS 3W?C /=-Rf H
dNX 3UKK NH6$ WBW<TCh R k QDUT 3%$ THC$ QDVR 3%$ THC$ YDYV 3%$ RHC$ VDTR 3+$ Q k SDRQ H6$
QHC$ VDVY 3+$ Q k SDTQ H6 QHC 00=f RTWyRHz dNX 3RKK NH6$ WBW<TCh
/ k RUDS$ QRDY$ LKDU$
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m'&&, %)<(+ 3QDVK 8$ LKM 2(&<+Cf XE k KDQS 3/5<)')*)'=J=&15.,)<$ LLhR$ >J>Cf =0
3/5<)')*)'=J=&15.,)<C QQV-QQS lWf N] 3A]ZC =J6 QVU aN n Hbnf ZX 3u_'C x k QQKY 3WdC$
R
RVRR 3W?C /=-Rf H dNX 3UKK NH6$ WBW<TCh R k QDYL 3%$ THC$ TDSL 3%$ THC$ YDYK 3%$ RHC$
YDLL 3+$ Q k SDLY H6$ QHC$ VDST 3+$ Q k SDLQ H6$ QHC 00=f HXN] 3A]ZC /.</7<.1&+ *)'
WRUHRQd?T]h QVUDKPTS aN n HbnD I)7,+ QVUDKPTP
^,P&(3.(3!*,N,U:%#$!*#$'(O,T,(W(,T@,3!.0",M,/0.1("'#.'*% UM7O= ^5(1& %)<(+ 3RDSS 8$
SQM 2(&<+Cf XE k KDPQ 3/5<)')*)'=J=&15.,)<$ LLhR$ >J>Cf =0 RVK-RVR lWf N] 3A]ZC =J6 QRK
aN n Hbnf ZX 3u_'C x k QQQP 3WdC$ RVQL 3W?C /=-Rf RH dNX 3UKK NH6$ WBW<TCh R k RDQS
RT
3+$ { kYDL H6$ YHC$ QDYQ 3%$ THC$ QDVY-QDST 3=$ RHC$ YDKL 3%$ RHC 00=f WyRHz dNX 3RKK
NH6$ WBW<TCh R k RUDY$ RLDS$ TTDV$ LKDS$ LSDK$ RRTDR$ RPVDV$ RVKDQ$ RVTDK 00=f HXN] 3A]ZC
/.</7<.1&+ *)' WRKHRQd?Q]h QRKDKPSL aN n HbnD I)7,+ QRKDKPSVD
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^,U)+.0",T,!*O,N,U:%#$!*#$'(O,T,(W(,T@,3!.0",M,/0.1("'#.'*% UM$O=NS/ g&<<)4 %)<(+ 3RDLL
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QRL lWf N] 3A]ZC =J6 QTU aN n Hbnf ZX 3u_'C x k QQRL 3WdC$ RVTQ 3W?C /=-Rf H dNX
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3UKK NH6$ WBW<TCh R k QDYL 3%$ THC$ YDYU 3+$ Q k RDLQ$ QHC$ VDYU 3+$ QHC 00=f HXN] 3A]ZC
/.</7<.1&+ *)'hWRRHSd?T]hQTUDKQQP aN n HbnD I)7,+ QTUDKQQTD
N,U:%#$!*#$'(O,T,(W(,^,U#$'(3$%",T,!*O,T@,3!.0",M,/0.1("'#.'*% UM'O=NS0 g&<<)4 %)<(+
3RDTY 8$ PKM 2(&<+Cf XE k KDTK 3/5<)')*)'=J=&15.,)<$ LLhR$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C
R
QPT-QPP lWf N] 3A]ZC =J6 QPK aN n Hbnf ZX 3u_'C x k QQKP 3WdC$ RVKU 3W?C /=-Rf H
dNX 3UKK NH6$ BN]?-4@Ch R k QDVL 3%$ THC$ VDRT 3%$ RHC$ VDTT 3++$ Q k TDLY H6$ PDKK H6C$
SDKP 3++$ Q k RDKL H6$ UDLY H6$ QHC$ SDRY 3++$ Q k RDRQ H6$ TDSP H6$ QHCf HXN] 3A]ZC
/.</7<.1&+ *)' WRRHVd?Q]Qh QULDLLLY aN n HbnD I)7,+ QULDLLLTD
N,U:%#$!*#$'(O,T,(W(,^,U3!.'4'",T,!*O,T@,3!.0",M,/0.1("'#.'*% UM@O=NS1 m'&2 %)<(+ 3RDQ 8$
UPM 2(&<+Cf XE k KDQS 3/5<)')*)'=J=&15.,)<$ LShQ$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C QKP-
R
QKSlWf N] 3A]ZC =J6 QUP aN n Hbnf ZX 3u_'C x k QQKY 3WdC$ RVQR 3W?C /=-Rf H dNX
3UKK NH6$ WBW<TCh R k QDVY 3%$ THC$ VDUT-VDUY 3=$ RHC$ VDPY 3%$ RHC$ VDSS 31+$ { k VDVV H6$
RDVP H6$ RHC$ SDKY-SDKL 3=$ RHC$ SDYS-SDVK 3=$ RHCf HXN] 3A]ZC /.</7<.1&+ *)'
WRQHSdQ?Q]h QUPDKTSP aN n HbnD I)7,+ QUPDKTSTD
N,U:%#$!*#$'(O,T,(W(,^,U3!.'4'",N,!*O,T@,3!.0",M,/0.1("'#.'*% UMEO=NS1 @(851 m'&2 %)<(+
3RDP 8$ PYM 2(&<+Cf XE k KDQQ 3/5<)')*)'=J=&15.,)<$ LShQ$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C
R
QKS-QRKlWf N] 3A]ZC =J6 QUP aN n Hbnf ZX 3u_'C x k QQRU 3WdC$ RVRY 3W?C /=-Rf H
dNX 3UKK NH6$ WBW<TCh R k QDVY 3%$ THC$ YDST 3%$ RHC$ VDYS-VDVK 3=$ QHC$ SDSR-SDSQ 3=$
QHC 00=f HXN] 3A]ZC /.</7<.1&+ *)' WRQHSdQ?Q]h QUPDKTSP aN n HbnD I)7,+ QUPDKTVSD
N,U:%#$!*#$'(O,^,U"03$#$0*%",T,!*O,T,(W(,T@,3!.0",M,/0.1("'#.'*% UM*O=NS/ F.<& 2&<<)4
%)<(+ 3QDPV 8$ SKM 2(&<+Cf XE k KDQS 3/5<)')*)'=J=&15.,)<$ LShQ$ >J>Cf =0
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3/5<)')*)'=J=&15.,)<C QUS-QPK lWf N] 3A]ZC =J6 QLU aN n Hbnf ZX 3u_'C x k QQRT 3WdC$
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RYLL 3W?C /=-Rf H dNX 3UKK NH6$ BN]?-4@Ch R k QDSV 3%$ THC$ VDTP 3%$ RHC$ VDYR-VDYL
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3=$ QHC$ SDKR 3+$ Q k VDVL H6$ RHC$ SDKV-SDRU 3=$ THC$ SDYP 3%$ RHC 00=f HXN] 3A]ZC
/.</7<.1&+ *)' WRVHRRd?Q]h QLUDKPSL aN n HbnD I)7,+ QLUDKPSYD
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^,UA"#$.0/%",c,!*O,N,U:%$#!*#$'(O,T,(W(,T@,3!.0",M,/0.1("'#.'*% UM:OD ?'.,8& %)<(+
3QDYT 8$ VKM 2(&<+Cf XE k KDPP 3/5<)')*)'=J=&15.,)<$ LLhR$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C
l
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QVK-QVR Wf N] 3A]ZC =J6 TUU aN n Hbnf ZX 3u_'C x k QQRK 3WdC $ RVTR 3W?C /=-Rf H
dNX 3UKK NH6$ WBW<TCh R k QDYR 3%$ THC$ YDYQ 3%$ RHC$ VDPQ-VDPL 3=$ UHC$ VDSS 3+$ { k SDP
NH6 QHC$ SDKV 3+$ { k SDRP NH6$ QHC$ SDYU 3%$ RHC 00=f RTWyRHz dNX 3RKK NH6$ WBW<TCh
R kRUDL$ RKYDR$ RRTDR$ RQUDT$ RQUDP$ RQPDS$ RQVDL$ RQLDK$ RTKDK$ RTKDL$ RTRDR$ RPVDS$ RYQDS$
RYLDY 00=f HXN] 3A]ZC /.</7<.1&+ *)'h WQRHRUd?Q]h TUUDKVUP aN n HbnD I)7,+ TUUDKVUYD
^,UN,/$*(.(3$%"!*O,T,(W(,N,U3'3%.'4'",S,!*O,T@,3!.0",M,/0.1("'#.'*% UN0O= ^5(1& %)<(+
3QQY =8$ VQM 2(&<+Cf XE k KDTP 3/5<)')*)'=J=&15.,)<$ LShQ$ >J>Cf =0 3/5<)')*)'=J=&15.,)<C
R
QQT-QQPlWf N] 3A]ZC =J6 TRP aN n Hbnf ZX 3u_'C x k QQRK 3WdC $ RYSK 3W?C /=-Rf H
dNX 3UKK NH6$ WBW<TCh R k RDSK 3%$ YHC$ TDSQ 3%$ UHC$ YDUT 3%$ RHC$ VDUQ-VDUU 3=$ QHC$
VDVQ-VDVU 3=$ QHC 00=f RTWyRHz dNX 3RKK NH6$ WBW<TCh R k QTDS$ QYDU$ PRDK$ VQDY$ LUDS$
RRVDQ$ RQPDY$ RQYDU$ RQVDP$ RQLDQ$ RQLDU$ RTSDQ$ RPLDV$ RYKDU$ RYQDQ 00=f HXN] 3A]ZC
/.</7<.1&+ *)'h WRVHRPW<dQ?Qh TRPDKLKK aN n HbnD I)7,+ TRPDKLKRD
^,UN,/$*(.(3$%"!*O,T,(W(,N,U3!..(*'4'",S,!*O,T@,3!.0",M,/0.1("'#.'*% UN1O=NS/ ?** 45(1&
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RYSQ 3W?C /=-Rf RH dNX 3UKK NH6$ BN]?-+YCh R k RDLU-RDLL 3=$ UHC$ TDVP 3%$ QHC$ TDLT
3QHC$ YDSU 3%$ RHC$ VDYK 3+$ Q k SDVU H6$ QHC$ VDLY 3+$ Q k SDYL H6$ QHC 00=f HXN] 3A]ZC
/.</7<.1&+ *)' WRYHRTW<dQ?Qh TKRDKVUU aN n HbnD I)7,+ TKRDKVUQD
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^,UN,1.(:(3$%"!*O,T,(W(,N,U3'3%.'4'",S,!*O,T@,3!.0",M,/0.1("'#.'*% UN/O=NS0 ?** 45(1&
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/ k QRDP$ QTDS$ QYDT$
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PKDS$ VQDR$ LTDS$ RRVDU$ RQYDR$ RQVDL$ RQLDV$ RUQDY$ RYKDV$ RYRDK$ RYQDY 00=f HXN] 3A]ZC
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The Journal of Organic Chemistry
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6D<P2
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3YC @($ ÄDf @(7$ gDf ]),8$ ÄDf ^.,8$ HDf m7$ HDf Å&,8$ HD Z,1&'/')%%&+ W.'E), d.,)'(,8% 4(15 F7'&
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3VC A5.'),$ ADf u.<(,.$ NDf I'&2$ mD @D Z,5(E(1(), )* A,&'82 G'.,%*&' E&14&&, W),`78.1&+ F)<2=&'
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The Journal of Organic Chemistry
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