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Satoshi Nakajima

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2010 12

Syntheses of Functional Molecules Bearing Hydrogen-Bonding Units

and their Supramolecular Polymers

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¶ Ò Ó z Ó z ¡ { ’ ) x í ’ 0 ( ´ ë Å ‰ Ó z r ' é n

 Š • ò Ý n  ô È a h à - i ! Ì Ò ) ñ Ò J ? Ò ø µ ö ’ ‡ € v  X l ¤ Ó z ¶ Ò v  H ø µ ö ’ ‡ € v  Y ô Ç Ô ] ¶ Ò Ó z 0  • - ¶ Ò Ó z Ó z 4 F V 9 [ H C X 8 ; V } ñ Ò v  ô * 2 0 k J / m o l Ó z ‚  1 0 M- 1 ­ , ¹ ‡ ) p H Ï  ð p » ‘ Ð x í Å Ó z Z à ÷ x Ø - ¶ Ò Ó z . + ¿  } é n  N U O [ u \ n  Ž + . ‘ Ð

’ ) ¬ ê ’ Š À ~ t û ³ ² Ø Ä Á ¦ ‹ . -

§ æ ž ² Ø ’ n  d Û   ø ¯ · ¾ è õ  û E B X 8 ; C T < 7 V n  ñ Ò ï œ Ø - N V J 1 U Y ` n  É Æ . + ² Ø ’ n  ¶ Ò Ó z 0 c é n  N U O [ ± Ñ 0 Æ ˜ q × E B X 8 ; C T < 7 V ñ Ò v  _ ƒ ø  $ ù l ¤ ø  ƒ 0 ¤ - É Æ T < 7 V ñ Ò v  L X B Y C D [ n  ô ¶ Ò Ó z Š • 0 ã

& + n  m Ü  E B X 8 ; C T < 7 V ð f 0 ( n  * " L X B Y C D [ ð f 0 ( n  — ˆ ¶ Ò Ó z 0 c   é n  N U O [ ± Ñ 0 Æ Å Œ × Ü  ¶ Ò Ó z S E ? B 0 ( ñ Ò x í Å

| Ù É x Ø N V J 1 U Y 0 z • . + é n  N U O [ + -   ß Ú ¨ Ÿ 0 š ®

§ æ ž Ă Í + ± • . , ü Í † æ ý Í E B X 8 ; C T < 7 V ñ Ò v  L X B Y C D [ n  ¶ Ò Ó z Š • 0 £ + þ Í n

 m Ü  E B X 8 ; C T < 7 V ð f * " L X B Y C D [ ð f 0 ¤ - n  0 z • é n  N U O [ 0 ± Ñ ÿ Í E B X 8 ; C T < 7 V ñ Ò v  n  m ¶ Ò Ó z 0 Š • - n  0   â á Z z • ¶ Ò Ó z Š • * - E B X 8 ; C T < 7 V ø  À ” ~ t ç æ Ā Í @ B T J 3 E V N V J 1 U Y ¶ Ò Ó z ¼ 0 ÿ j ( n  - S W 2 C I U P A 1 G Y

( U P y )0 „ k   ß N V J 1 U Y ä „ g 0 z • N V J 1 U Y ä „ g N U 4

> W Y K > W Y 0 = M [ : U P y` Õ › N U 4 > W Y K > W Y é n  N U O [ ì # ā Í U P y 0 „ k N V J 1 U Y * " N U 4 >

W Y K > W Y º ¸ + N V J 1 U Y é n  + • - Ú 0 h • R V J 5 X <

[ 0 à ª Ă Í • « 0 w , % ' § n ó b Œ 0 … ¥ y Í ° Ý e ^ , -

Î ü Í ù l ¤ Ó z ¿ ¶ Ò Ó z ½ ¼ 0 / ¶ Ò Ó z 0 ú s r - é n  N U O [ ’ è  © Ê Þ 0 ° å % l ¤ Ó z * z • . ¢ Ê E B X ; C T < 7 V ) N V J 1 U Y ± î g 0 o ™ ¿

 + § æ ž – é n  N U O [ f Õ “ Ö 0 æ ì

Î ý Í E B X 8 ; C T < 7 V n  L X B Y C D [ n  ¶ Ò Ó z Š

• ç æ T < 7 V Ë 2 , 2 , 6 , 6 -@ B T Q > V I M U < E V-N-6 8 ;

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ëì2

V( T E M P O ) F X = Y > ? [ m | D + A [ V " * W ( Ð ‚ d ' Ü ‘

@ = X 0 3 > T 4 . V m | F X = Y > ? [ m | ¥ º ¼ v ‰  ' , W 1 = X 5 F W [ ) - Y r Ò ß m Ÿ( E S I - M S ) " $ ¡ Ï ª } † ) - Y r

" % Ò ß m Ÿ ¨ $ ¥ º ¼ v ' z m | ß ¡ l u à %

T E M P O D + A [ V 1 X X J V N/O 8 A [ V « © E S I - M S ª } ^ Â

_ ß d ³ ˆ % m | ß ¡ l & @ = X 0 3 > T 4 . V m | F X = Y > ? [ m | ¥ º ¼ v ‰  ' n ~ Ï T E M P O D + A [ V 1 X X J V N « © Ó { m h @ = X 0 3 > T 4 . V N - O " D + A [ V Ð ‚

d O - H b ¿ ” q Ó Æ 3 D = Ì ª & @ = X 0 3 > T 4 . V Þ º s |

F X = Y > ? [ m | ¥ º ¼ v ' ‰  % ' › # É ¤ ’ – ¨ e  T E M P O 4 , 4 ’ -4 B > X 0 3 4 D + @ V O 8 Y # % ¼ œ X ¾ ¢ Û Í Ÿ @ = X 0 3 > T 4 . V N - O ¼ v Õ ä T E M P O N - O ¼ v Õ ä " $ ¹ 0 . 1 Å à $ ¥ º ¼ v ‰  ' • “ T E M P O 5 C Y  … s | å È m ƒ ' ¦ % X ¾ ¼ œ ¢ Û Í Ÿ < [ 8 ' ! G a u s s i a n

 … § ⠗ ¨ " % m | 3 M R W [ 3 S Y ! ~ š ¥ º ¼ v ' ‰  % " $ @ = X 0 3 > T 4 . V Ý c ´ º s | ] 5 C Y  … g $ Þ º s |

" $ Ñ å È ' „ ¢ Û ' % ' Ë l

¶ é µ @ = X 0 3 > T 4 . V Ý c ' m | k Ê — f ! m | ' ˜ v

 ¥ º ¼ v ' ` E X = Y > ? [ m | Ô m | K U L [ ¢ · Î Ù 1 , 3 , 5 -= U 5(E X P O 9 V)H Y 7 Y ' l ± ­ Ò Wi l l i a m s o n t Œ " $ T E M P O Ý c ' é f ‚ i 1 , 3 , 5 -= U 5( 2 ’ , 2 ’ , 6 ’ , 6 ’ -; = T O 9 V C I U 4 Y-N-- 0 3 V- 4 ’ -, [ ; V)O 9 V H Y 7 Y ' ‹ 1 , 3 , 5 -= U 5( 2 ’ , 2 ’ , 6 ’ , 6 ’ -;

= T O 9 V C I U 4 Y-N-- 0 3 V- 4 ’ -, [ ; V)O 9 V H Y 7 Y D + A [ V Ð

‚ d = U B > X 0 3 = U D + @ V O 8 Y ' P V £ 1 : 1 O 8 A [ V « Í Š / T 5 ; D X Y ž ] > X : F 0 Q 5 = ¨  Ä Ô m | Ä # Ô m | Ä ' 1 0 0 p ¬ Z » ¸ % À ½ ®   Ö ¢ Û d ! ‹ % X ¾ x  ª } / T 5 y ž ] Ô m | Ä 2θ = 1 5 ° ( d = 5 . 9 Å ) a Ø E X [ > C [ 1 Ì ª & Ô m | æ œ Ò À ½ ® Ž À ½ × ™ w 2θ = 1 6 . 4 ° , 2 5 . 3 ° ‡ C [ 1 Ì ª &  Œ % ç á ã

d 5 . 4 1 , 3 . 5 1 Å & & F X = Y ( 1 6 F 8 [ m | > ? [ m | á π 5 8

: 0 Y 2 Õ ä \ Å { o " $ 1 , 3 , 5 -= U 5( 2 ’ , 2 ’ , 6 ’ , 6 ’ -; = T O 9 V C I U 4 Y-N-- 0 3 V- 4 ’ -, [ ; V)O 9 V H Y 7 Y \ Ý . T N ¢ Û ' ‰  À

½ Á # & % ¥ º ¼ v ! u Ú  Z ™ w  Ç è ¯ π 5 8 : 0 Y 2 ^  " $ ¬ u Ú ² Ô m | K U L [ °  Á €

¶ ê µ @ = X 0 3 > T 4 . V m | k ¥ º ¼ v ' ‰  % 4 - (N-t e r t- E 9 V-N-( M A 0 3 V) - 3 -G 0 3 V ( M > -t e r t -E 9 V H Y 7 Y ' ˜ v  @ = X 0 3 > T 4 . V æ j  å |  m | k ¥ º ¼ v Ó { m h ¨ "

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+ N - O m Û ¥ } ì à = M G * “ è Ă  ? L ` w Ć ? P 9 G ] f –

Ă  † ‚ M 3 J ] O _ G ` ) + î ž × µ ò . g - ) + Ó z ž × Ù „ ’ ª * f – Ă   € ï ô {  v p " £ + . ­ *

Ò Ċ Ð U P y . E G [ M 3 J ] S ] M 0 \ ` ˜ u U P y j Ü ¦ S ] M 0 \ ` . „ ¡ E G [ M 3 J ] S ] M 0 \ ` . z Å Á ë k Ë ÷ I G \ 2 V ) + J G _ ~  Œ ~ ? @ J G _ ‹ . õ t / U K j Ü ¦ S ] M 0 \

` 7 ] R J ] > 1 U B A b ] ) + ¼   ~ U P y / U K j Ü ¦ S ] M 0 \ ` . 9 _ _ Q ] V i Ø  ¨ ¢ U P y j Ü ¦ S ] M 0 \ ` . „ ¡

* S ] M 0 \ ` i Ÿ ù š 1 6 `(k ú û ) ! Æ ù). ˜ u U P y j Ü ¦ ù š S ] M 0 \ ` S \ 4 C ^ ` N C ^ ` . ? P b < h ± Ñ Z ^ 1 H L \ U F 0 K ` . ' U P y j Ü ¦ S \ 4 C ^ ` N C ^ ` ' „ ¡ U P y j Ü ¦ S ] M 0 \ ` ) ! S \ 4 C ^ ` N C ^ ` 9 _ _ Q ] V À ¾ * î {  S

\ T b . ß Å Ç Ä ¡ S ] M 0 \ ` î {  S \ T b ¹ Ö Ù „ æ ã & ¬ ‘ {  ø ¿ ’(; ] ½ ñ 9 _ T G : [ M 0 b ) {  ø Ó z ‡ ā j · t N M RaD O S Y » ) + º ’ £ © r ª * {  ø . Ó z S ] M 0 \ ` î {  S \ T b {  ø . ĉ Ĉ d l e ä Í Ò ċ Ð U P yj Ü ¦ S ] M 0 \ ` S \ 4 C ^ ` N C ^ ` * , î {  Þ q ¡ X ] M 5 _ > b ê é U P y j Ü ¦ S ] M 0 \ ` ) ! S \ 4 C ^ ` N C ^ ` . Ì … ¯ ¸ 9 _ _ Q ] V ) ! G ] 4 ` À æ H _ D O 8 Y ? G » ) + ¡ Þ S ] M 0 \ ` … ¯ ø ® Ž č Ĉ ć ß Ï Þ . q ¡ S ] M 0 \ ` î {  Þ X ] M 5 _ > b .   ý | Ą ž ü( A F M ) ) ! ñ ó Š Ă  Ą ž ü( T E M ) å • î {  Þ â ă A F M s o § Å   G ] 4 ` À ¾ * Ä ¡ Þ 2 03 0 n m ý þ ­ É U 9 _ È { Ā . › ¡ o § Å À  ¹ Ö Ù „ y µ Ô í + ( Ą á È { Ā µ ò î {  Þ « ă T E M s ' # $ ‰ c Õ 2 0 n m œ H D G  H W 1 ` . å ¿ Þ x ö % È { Ā µ ò £ , . ­ * S ] M 0 \ ` ¹ Ö Ù „ . ą } | ” ‘ ˆ , H W 1 ` . › ¡ , î {  Þ q ¡ . ƒ Ý

Ò Č Ð l e Ê Î Ú ¤ — ³ ™ ° , ¶ Ý   {  ¹ Ö Ù „ . ą } | {  ÿ „ , / O _ b C ‹ î {  S \ T b Ä ¡ . “ à ² Ê Î

¡ ´ . Ú ¤ î {  S \ T b n Ü — ³ ™ ° . ç ð

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1. (!-)

“Intermolecular Hydrogen-Bonding of Nitroxide Radicals with Proton-Donating Molecules and their Supramolecular Polymers”

Journal of the American Chemical Society, (+=)

Satoshi Nakajima, Eisuke Kato, Masayuki Minatozaki, Hiroyuki Nishide

2. (L!)

“Synthesis of Metalloporphyrins Bearing Quadruply Hydrogen-Bonding Units and their Supramolecular Membrane”

Organic Letter, (+=)

Satoshi Nakajima, Haruki Ohkawa, Hiroyuki Nishide

3. (!-)

“A Supramolecular Polymer of Nitroxide Radicals via Hydrogen Bonding”

Macromolecular Symposia, (,K4')

Satoshi Nakajima, Eisuke Kato, Masayuki Minatozaki, Hiroyuki Nishide

4. (!-)

53?@ J$

, 19 (,K4') ( CF &

5. (L!)

“Cyclic Tetramer of a Metalloporphyrin Based on a Quadruple Hydrogen Bond”

Organic Letter, 8, 2225-2228 (2006)

Haruki Ohkawa, Akihiro Takayama, Satoshi Nakajima, Hiroyuki Nishide

6. (L!)

“Covalent Fixation of the Cyclic Tetramer of a Metallo-porphyrin Based on Self-complementary Quadruple Hydrogen Bonding”

Chemistry Letter, 35, 1076-1077 (2006)

Haruki Ohkawa, Akihiro Takayama, Satoshi Nakajima, Hiroyuki Nishide

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1. e ,j,7%

S59)m ,^a (2010. 9, ?3) 0 XG1 M[] /

2. Supramolecular Polymer of Nitroxide Radicals via Hydrogen Bonding and its Properties 5th IUPAC International Symposium on Macro- and Supramolecular Architectures and Materials (2010. 8, Ocho Rios, Jamaica)

Satoshi Nakajima, Masayuki Minatozaki, Hiroyuki Nishide 3. ETU&e , S59)m ,.4D+ (2010. 5, CF)

0 XG1 M[] /

4. ETU&e ,Bg 9>#.S90);-4 (2010. 3, +i)

0 XG1 M["Z Yc@1 h] /

5. Supramolecular Polymer of Nitroxide Radicals via Hydrogen Bonding

13th IUPAC International Symposium on Macromolecular Complexes (2009. 11, Concepcion, Chile)

Satoshi Nakajima, Eisuke Kato, Masayuki Minatozaki, Hiroyuki Nishide

6. Quadruply Hydrogen-Bonded Supramolecular Polymer Based on a Porphyrin The 1st FAPS Polymer Congress (2009. 10, Nagoya)

Satoshi Nakajima, Hiroyuki Nishide

7. ETU&e ,j,7%

S58)m ,^a (2009. 9, I>)

0 X"Z YcG1 M[] /

8. ETU&e ,j,7%

S58)m ,.4D+ (2009. 5, O6) 0 X"Z Yc] /

9. ETU&e ,5d S57)m ,^a (2008. 9, +i)

0 X"Z YcG1 M[] /

10. Supramolecular Nitroxide Radical Polymer via Hydrogen Bonding

4th IUPAC-Sponsored International Symposium on Macro- and Supramolecular Architectures and Materials (2008. 9, Düsseldorf, Germany)

Satoshi Nakajima, Eisuke Kato, Hiroyuki Nishide

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qr

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Qm( l, O^O]=fa, O^O];B i,YoNbY-p

11. IUV+ C X>+<

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12. Supramolecular Porphyrin Copolymer Formed with a Quadruply Hydrogen Bonding Macromolecules for a Safe, Sustainable, and Healthy World (2007. 6, New York, USA).

Satoshi Nakajima, Haruki Ohkawa, Hiroyuki Nishide

13. .LIUV+e'2+<kU%jgh T55/n'2`c# (2006. 9, 57)

!8 Z19 @G_& 4"

参照

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